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99-76-3

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  • CAS 99-76-3 low price methyl 4-hydroxybenzo /methyl p-hydroxybenzoate

    Cas No: 99-76-3

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99-76-3 Usage

Chemical properties

Methylparaben is a colourless crystalline powder that is odourless or has a faint characteristic odour and a slight burning taste. Slightly soluble in water, easily soluble in ethanol, ether, acetone and other organic solvents.One gram dissolves in 2.5 ml ethanol, in about 4 ml of propylene glycol, and in 400 ml of water at 25°C or about 50 ml of water at 80 a C. It is permissible at levels up to 0.1 % in soft drinks, non-leavened bakery products, and other products where it is generally used as a fungistat. From 1000 to 4000 ppm are required to inhibit Gram-positive bacteria. Like the benzoates, its effectiveness increases with decreasing pH.Methylparaben can by assayed by placing 2 g in a flask and adding 40.0 ml of I N NaOH (with rinsing of sides of flask with water). With a watch glass cover in place, boil gently for I h and cool. Add five drops of bromthymol blue T.S., and titrate the excess NaOH with 1 N H2S04 to pH 6.5 by matching the colour of pH 6.5 phosphate buffer containing the same proportion of indicator. Each ml of 1 N NaOH = 152.2 mg of methylparaben (National Academy of Sciences, 1963).

Uses

Different sources of media describe the Uses of 99-76-3 differently. You can refer to the following data:
1. Methylparaben is the ester of methyl alcohol and p-hydroxybenzoic acid, It is a bacteriostatic agent and preservative that was added to local anesthetic agents without vasoconstrictors before 1984 to prevent bacterial growth.Allergic reactions developed from repeated exposures to parabens led to the removal of this agent from dental anesthetic solutions.Similar products produced by similar production methods, like ethyl p-hydroxybenzoate (paraben B) and propyl p-hydroxybenzoate (Nepalese c), are also disinfectant preservatives.The products are irritating to the skin.
2. parabens is one of the most commonly used group of preservatives in the cosmetic, pharmaceutical, and food industries. Parabens provide bacteriostatic and fungistatic activity against a diverse number of organisms, and are considered safe for use in cosmetics, particularly in light of their low sensitizing potential. An evaluation of preservatives for use in leave-on cosmetic preparations lists parabens among the least sensitizing. The range of concentrations used in cosmetics varies between 0.03 and 0.30 percent, depending on the conditions for use and the product to which the paraben is added.Methylparaben is one of the most popular preservatives in beauty products and food items. According to the National Library of Medicine, the ingredient occurs naturally in a handful of fruits—like blueberries—though it can also be created synthetically.It's found in everything from cream cleansers and moisturizers to primers and foundations and helps these products maintain their effectiveness. Rabach says that it's chock-full of anti-fungal and antibacterial properties, which work wonders to extend the shelf life of skincare, haircare, and cosmetic products.https://www.byrdie.com/methylparaben-for-skin-4779820
3. Methylparaben is an antimicrobial agent which is a white free-flowing powder. it is active against yeast and molds over a wide ph range. see parabens.
4. Methyl 4-hydroxybenzoate is used as an anti-fungal agent. It is also used as a preservative in foods, beverages and cosmetics. It acts as an inhibitor of growth of molds and to lesser extent bacteria and as a vehicle for ophthalmic solution.

Content analysis

Method one: determinate according to the content analysis method in "butyl p-hydroxybenzoate (07002)". Per mL 1 mol/L sodium hydroxide is equivalent to the product (C8H8O3) 152.2mg. Method two: Take 0.1 g (accurate to 1 mg) of the sample previously dried on silica gel for 5 h and move into a 300 ml flask with a glass plug. Plus l mol/L sodium hydroxide 10ml, heated in the water bath for 15min. After cooling, add 0.1mol/L potassium bromate 0.00ml, potassium bromide 5.0g and l mol/L hydrochloric acid 30ml. Put 15min in the dark room after sealing. Add potassium iodide 1 g, shake the flask vigorously, with 0.1mol/L sodium thiosulfate titration, with starch test solution (TS-235) as an indicator. Per ml 0.1mol/L potassium bromate is equivalent to the product (C8H8O3) 25.36mg.

Toxicity

ADI 0~10mg/kg(FAO/WHO,2001). GRAS(FDA,§184.1490,2000). LD503000mg/kg(Dog, mouth)

Utilization limitation

FAO/WHO (1984): Jam, jelly, 1000mg/kg (single or with benzoate, sorbic acid and potassium sorbate). EEC(1990,mg/kg): For use in pigment solutions, flavor syrups, coffee extracts, frozen drinks, fruit, glucose and soft drinks, pickled fish, salad, sauce, snack food, concentrated soup and so on, limited to GMP; Beer 70; Snack cereals and soup concentrate 175, the same as "07018 p-hydroxybenzoate". HACSG is listed as a restricted list. FDA,§184.1490(2000):0.1%.

Preparation

Different sources of media describe the Preparation of 99-76-3 differently. You can refer to the following data:
1. The drug is esterified with p-hydroxybenzoic acid and methanol. The p-hydroxybenzoic acid was added to excess methanol to dissolve, stirring and adding concentrated sulfuric acid slowly. After heating and refluxing 10h, pour into the water to precipitate crystallization, then washed with water, sodium carbonate solution and water, finally obtain the crude product. Recrystallize from water or 25% ethanol to obtain finished product. The yield was 85%. Raw material consumption (kg/t): p-hydroxybenzoic acid 1200, methanol 1000.
2. Produced by the methanol esterification of p-hydroxybenzoic acid in the presence of sulfuric acid. The materials are heated for distillation in a glass-lined reactor under reflux. The acid is then neutralized with caustic soda and the product is crystallized by cooling. The crystallized product is centrifuged, washed, dried under vacuum, milled and blended, all in corrosion-resistant equipment to avoid metallic contamination.

Acute toxicity

Abdomen-mouse LD50: 960 mg/kg

Flammability hazard characteristics

Combustible, excretes spicy smoke from fireground

Storage

Ventilated , low temperature and dry warehouse.

Chemical Properties

Different sources of media describe the Chemical Properties of 99-76-3 differently. You can refer to the following data:
1. Methylparaben occurs as colorless crystals or a white crystalline powder. It is odorless or almost odorless and has a slight burning taste. Soluble in alcohol,ether; slightly soluble in water, benzene, and carbontetrachloride.
2. Methyl p-hydroxybenzoate is odorless or has a faint characteristic odor and a slight burning taste. Methyl p-hydroxybenzoate is more commonly known as methyl paraben and is an ester of p-hydroxybenzoic acid.

Occurrence

Reported present in cloudberry, yellow passion fruit juice, white wine, botrytised wine and Bourbon vanilla.

Definition

ChEBI: A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blu berries.

Production Methods

Methylparaben is prepared by the esterification of p-hydroxybenzoic acid with methanol.

Aroma threshold values

Detection: 2.6 ppm.

General Description

Methyl paraben is basically a methyl ester of p-hydroxybenzoic acid. It is non-toxic, and non-carcinogenic in nature. It is a stable, non-volatile compound and finds application as an anti-microbial preservative in foods, drugs and cosmetics. It is readily absorbed through the skin and gastrointestinal tract. Upon hydrolyzation, it is hydrolyzed to p-hydroxybenzoic acid, and the conjugates formed get rapidly excreted in the urine.

Hazard

Toxic. Use in foods restricted to 0.1%.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Methylparaben is widely used as an antimicrobial preservative in cosmetics, food products, and pharmaceutical formulations; see Table I. It may be used either alone or in combination with other methylparaben is the most frequently used antimicrobial preservative. The parabens are effective over a wide pH range and have a broad spectrum of antimicrobial activity, although they are most effective against yeasts and molds. Antimicrobial activity increases as the chain length of the alkyl moiety is increased, but aqueous solubility decreases; therefore a mixture of parabens is frequently used to provide effective preservation. Preservative efficacy is also improved by the addition of propylene glycol (2–5%), or by using parabens in combination with other antimicrobial agents such as imidurea; Owing to the poor solubility of the parabens, paraben salts (particularly the sodium salt) are more frequently used in formulations. However, this raises the pH of poorly buffered formulations. Methylparaben (0.18%) together with propylparaben (0.02%) has been used for the preservation of various parenteral pharmaceutical formulations;

Biochem/physiol Actions

Methyl 4-hydroxybenzoate, also called methyl paraben or nipagin, comprises the ester of p-hydroxybenzoic acid. It is present naturally in cloudberry, white wine and bourbon vanilla. Methyl 4-hydroxybenzoate has antimicrobial and antifungal functionality and is commercially used as a preservative in the food, cosmetic and pharmaceutical industry. Methyl 4-hydroxybenzoate has cytotoxic effects on keratinocytes in the presence of sunlight. Methyl 4-hydroxybenzoate upon solar irradiation mediates DNA damage and modulates esterase metabolism resulting in skin damage and favors cancer progression. Methyl 4-hydroxybenzoate has estrogenic functionality and upregulates estrogen-related genes.

Safety

Methylparaben and other parabens are widely used as antimicrobial preservatives in cosmetics and oral and topical pharmaceutical formulations. Although parabens have also been used as preservatives in injections and ophthalmic preparations, they are now generally regarded as being unsuitable for these types of formulations owing to the irritant potential of the parabens. These experiences may depend on immune responses to enzymatically formed metabolites of the parabens in the skin. Parabens are nonmutagenic, nonteratogenic, and noncarcinogenic. Sensitization to the parabens is rare, and these compounds do not exhibit significant levels of photocontact sensitization or phototoxicity. Hypersensitivity reactions to parabens, generally of the delayed type and appearing as contact dermatitis, have been reported. However, given the widespread use of parabens as preservatives, such reactions are relatively uncommon; the classification of overstated. Immediate hypersensitivity reactions following injection of preparations containing parabens have also been reported. Delayed-contact dermatitis occurs more frequently when parabens are used topically, but has also been reported to occur after oral administration. Unexpectedly, preparations containing parabens may be used by patients who have reacted previously with contact dermatitis provided they are applied to another, unaffected, site. This has been termed the paraben paradox. Concern has been expressed over the use of methylparaben in infant parenteral products because bilirubin binding may be affected, which is potentially hazardous in hyperbilirubinemic neonates. The WHO has set an estimated total acceptable daily intake for methyl-, ethyl-, and propylparabens at up to 10 mg/kg bodyweight. LD50 (dog, oral): 3.0 g/kg LD50 (mouse, IP): 0.96 g/kg LD50 (mouse, SC): 1.20 g/kg

Carcinogenicity

The carcinogenic potential of methyl paraben has been studied in rodents. Several studies are available, but none that expose animals via oral or dermal routes. No evidence of a carcinogenic effect was observed following intravenous or subcutaneous injection .

storage

Aqueous solutions of methylparaben at pH 3–6 may be sterilized by autoclaving at 120°C for 20 minutes, without decomposition. Aqueous solutions at pH 3–6 are stable (less than 10% decomposition) for up to about 4 years at room temperature, while aqueous solutions at pH 8 or above are subject to rapid hydrolysis (10% or more after about 60 days storage at room temperature);Methylparaben should be stored in a well-closed container in a cool, dry place.

Purification Methods

Fractionally crystallise the ester from its melt, and recrystallise it from *benzene, then from *benzene/MeOH and dry it over CaCl2 in a vacuum desiccator. [Beilstein 10 IV 360.]

Incompatibilities

The antimicrobial activity of methylparaben and other parabens is considerably reduced in the presence of nonionic surfactants, such as polysorbate 80, as a result of micellization.However, propylene glycol (10%) has been shown to potentiate the antimicrobial activity of the parabens in the presence of nonionic surfactants and prevents the interaction between methylparaben and polysorbate 80. Incompatibilities with other substances, such as bentonite, magnesium trisilicate,talc,tragacanth,sodium alginate, essential oils,sorbitol,and atropine,have been reported. It also reacts with various sugars and related sugar alcohols. Absorption of methylparaben by plastics has also been reported; the amount absorbed is dependent upon the type of plastic and the vehicle. It has been claimed that low-density and high-density polyethylene bottles do not absorb methylparaben. Methylparaben is discolored in the presence of iron and is subject to hydrolysis by weak alkalis and strong acids.

Regulatory Status

Methylparaben and propylparaben are affirmed GRAS Direct Food Substances in the USA at levels up to 0.1%. All esters except the benzyl ester are allowed for injection in Japan. In cosmetics, the EU and Brazil allow use of each paraben at 0.4%, but the total of all parabens may not exceed 0.8%. The upper limit in Japan is 1.0%. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM, IV, and SC injections; inhalation preparations; ophthalmic preparations; oral capsules, tablets, solutions and suspensions; otic, rectal, topical, and vaginal preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 99-76-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 99-76:
(4*9)+(3*9)+(2*7)+(1*6)=83
83 % 10 = 3
So 99-76-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O3/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4,9H,1H3,(H,10,11)/p-1

99-76-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (H0216)  Methyl 4-Hydroxybenzoate  >99.0%(HPLC)(T)

  • 99-76-3

  • 25g

  • 150.00CNY

  • Detail
  • TCI America

  • (H0216)  Methyl 4-Hydroxybenzoate  >99.0%(HPLC)(T)

  • 99-76-3

  • 500g

  • 515.00CNY

  • Detail
  • Supelco

  • (47889)  MethylParaben  analytical standard

  • 99-76-3

  • 000000000000047889

  • 208.26CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1012)  Methylparaben  pharmaceutical secondary standard; traceable to USP and PhEur

  • 99-76-3

  • PHR1012-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1012)  Methylparaben  pharmaceutical secondary standard; traceable to USP and PhEur

  • 99-76-3

  • PHR1012-10G

  • 4,312.04CNY

  • Detail
  • Sigma-Aldrich

  • (M1650000)  Methylparahydroxybenzoate  European Pharmacopoeia (EP) Reference Standard

  • 99-76-3

  • M1650000

  • 1,880.19CNY

  • Detail
  • USP

  • (1432005)  Methylparaben  United States Pharmacopeia (USP) Reference Standard

  • 99-76-3

  • 1432005-125MG

  • 3,720.60CNY

  • Detail
  • Sigma-Aldrich

  • (M8911)  Methyl4-hydroxybenzoate  analytical standard

  • 99-76-3

  • M8911-1VL

  • 1,350.18CNY

  • Detail
  • Sigma-Aldrich

  • (M8911)  Methyl4-hydroxybenzoate  analytical standard

  • 99-76-3

  • M8911-5VL

  • 4,998.24CNY

  • Detail

99-76-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methylparaben

1.2 Other means of identification

Product number -
Other names methyl 4-hydroxybenzoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:99-76-3 SDS

99-76-3Synthetic route

methanol
67-56-1

methanol

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid for 8h; Heating;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; chemoselective reaction;100%
methyl 4-acetoxybenzoate
24262-66-6

methyl 4-acetoxybenzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h;100%
With phosphate buffer In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;100%
With ammonium acetate In methanol at 20℃; for 2.5h;100%
methanol
67-56-1

methanol

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With oxygen at 80℃; under 3750.38 Torr; for 4h; Temperature; Reagent/catalyst; Pressure; Sealed tube;99.3%
With perchloric acid; sodium percarbonate; vanadia for 1h; Cooling;98%
With perchloric acid; dihydrogen peroxide; vanadia In water at 5℃; for 2.5h; oxidative esterification;97%
methyl iodide
74-88-4

methyl iodide

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;99%
Stage #1: 4-hydroxy-benzoic acid With sodium hydrogencarbonate In water at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;
95%
With potassium hydroxide at 220℃; im geschlossenen Rohr;
With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics;
methyl 4-(cyanomethoxy)benzoate
137988-24-0

methyl 4-(cyanomethoxy)benzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethanol99%
methyl 4-allyloxybenzoate
35750-24-4

methyl 4-allyloxybenzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 0.333333h;99%
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;95%
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;95%
4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester
133642-20-3

4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetonitrile at 20℃; for 0.166667h;99%
With potassium hydroxide In ethanol at 20℃; for 0.7h;95%
With sodium phosphate dodecahydrate In N,N-dimethyl-formamide at 20℃; for 2h; chemoselective reaction;92%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

4-Iodophenol
540-38-5

4-Iodophenol

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;99%
With triethylamine at 80℃; under 3750.38 Torr; for 3h; Autoclave;75%
With triethylamine; G0-C2 PAMAM dendrimer*PPh2*PdMe2 at 105℃; under 5171.62 Torr; for 19h;100 % Chromat.
4-carbomethoxyphenyl triflate
17763-71-2

4-carbomethoxyphenyl triflate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h;99%
With caesium carbonate In toluene at 80℃; for 15h;87%
With ammonium acetate; methanol; magnesium; palladium on activated charcoal at 20℃; for 24h;51%
With (1,2-dimethoxyethane)dichloronickel(II); N-isopropyl-N-tert-butylamine; N-tert-butoxycarbonyl-proline; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 40℃; for 14h; Irradiation; Sealed tube;27 %Spectr.
4-benzyloxy-benzoic acid methyl ester
32122-11-5

4-benzyloxy-benzoic acid methyl ester

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 44h; Inert atmosphere; Schlenk technique; Irradiation;99%
With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 0.333333h;97%
With thiophene; sodium hydrogen sulfate; silica gel for 6h; Heating;96%
potassium (4-(methoxycarbonyl)phenyl)trifluoroborate
705254-34-8

potassium (4-(methoxycarbonyl)phenyl)trifluoroborate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;99%
4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 48h; Reagent/catalyst; Irradiation; Green chemistry;99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 28h; Irradiation;99%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; under 760.051 Torr; for 27h; Irradiation; Green chemistry;98%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere;98%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;92%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;79%
dihydrogen peroxide
7722-84-1

dihydrogen peroxide

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;98%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With sulfuric acid at 80 - 85℃; for 7.5h; Neat (no solvent); chemoselective reaction;97.6%
With NaY faujasite at 165℃; for 24h;87%
dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;97%
methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
171364-80-0

methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With water; caesium carbonate; hydrazine hydrate at 80℃; for 24h;97%
With air at 25℃; for 16h; Inert atmosphere;25 mg
With Oxone; potassium phosphate; naphthalene-2-boronic acid In water at 70℃; for 1h; chemoselective reaction;
4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester
133642-20-3

4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester

Cs2CO3

Cs2CO3

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃; for 1h;96%
4-(methoxymethoxy)benzoic acid methyl ester
139884-19-8

4-(methoxymethoxy)benzoic acid methyl ester

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1h;96%
4-allyloxycarbonyloxybenzoic acid methyl ester
1333925-55-5

4-allyloxycarbonyloxybenzoic acid methyl ester

2-propanethiol
75-33-2

2-propanethiol

A

allylisopropyl sulfide
50996-72-0

allylisopropyl sulfide

B

carbon dioxide
124-38-9

carbon dioxide

C

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With Roussin's red salt ester; tetrabutylammomium bromide; potassium hydride In tetrahydrofuran; ethanol at 40℃;A n/a
B n/a
C 96%
methanol
67-56-1

methanol

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With palladium 10% on activated carbon; oxygen; sodium carbonate at 120℃; under 15001.5 Torr; for 1.5h; Microwave irradiation; Green chemistry;96%
With sodium carbonate; palladium; silver(l) oxide at 80℃; for 48h; Molecular sieve;85%
With oxygen at 79.84℃; under 3750.38 Torr; for 12h; Autoclave;
3-iodo-4-methoxy-benzoic acid methyl ester
35387-93-0

3-iodo-4-methoxy-benzoic acid methyl ester

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane; ethanethiol for 6.5h; temp. 0 deg C -> RT;95.1%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;94%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;89%
With nickel(II) sulphate; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 12h; pH=8.8; UV-irradiation; Inert atmosphere; Glovebox; Enzymatic reaction;85%
methyl 4-acetoxybenzoate
24262-66-6

methyl 4-acetoxybenzoate

A

4-acetyloxy-benzoic acid
2345-34-8

4-acetyloxy-benzoic acid

B

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; 2-amino-benzenethiol at 100℃; for 0.75h; Hydrolysis;A 7%
B 93%
4-(tert-butoxycarbonyloxy)benzoic acid methyl ester

4-(tert-butoxycarbonyloxy)benzoic acid methyl ester

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With methanol; carbon tetrabromide; triphenylphosphine for 18h; Reflux;93%
With piperidine In dichloromethane at 20℃; for 4h;92%
oxygen
80937-33-3

oxygen

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;93%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
microwave irradiation;92%
methanol
67-56-1

methanol

Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With lanthanum complex grafted upon hydrotalcite for 8h; pH=10; Reflux;92%
scandium tris(trifluoromethanesulfonate) at 64℃; for 168h;81%
With C7H10N2O2*Zn(2+)*2C7H9N2O2(1-)*H2O at 75℃; for 24h; Catalytic behavior;54 %Spectr.
4-benzoyloxybenzoic acid methyl ester
75915-29-6

4-benzoyloxybenzoic acid methyl ester

A

4-(benzoyloxy)benzoic acid
28547-23-1

4-(benzoyloxy)benzoic acid

B

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; 2-amino-benzenethiol at 100℃; for 0.75h; Hydrolysis; debenzoylation;A 9%
B 91%
benzyl chloride
100-44-7

benzyl chloride

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-benzyloxy-benzoic acid methyl ester
32122-11-5

4-benzyloxy-benzoic acid methyl ester

Conditions
ConditionsYield
With iodide; potassium carbonate In acetone for 7h; Reflux;100%
With sodium methylate
With sodium ethanolate
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

allyl bromide
106-95-6

allyl bromide

methyl 4-allyloxybenzoate
35750-24-4

methyl 4-allyloxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 65℃; for 20h;100%
With potassium carbonate In dimethyl sulfoxide at 20℃; for 8h;99%
With potassium carbonate In acetone Heating;89%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 3-bromo-4-hydroxybenzoate
29415-97-2

methyl 3-bromo-4-hydroxybenzoate

Conditions
ConditionsYield
With ammonium metavanadate; aluminum tri-bromide; oxygen In 1,4-dioxane at 80℃; for 18h;100%
With bromine In acetic acid Ambient temperature;99%
With bromine In dichloromethane at 20℃; for 24h;95%
1-undecen-11-ylbromide
7766-50-9

1-undecen-11-ylbromide

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-undec-10-enyloxybenzoic acid methyl ester
59100-35-5

4-undec-10-enyloxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetonitrile at 70℃; Inert atmosphere;
Stage #2: 1-undecen-11-ylbromide In acetonitrile for 12h; Reflux; Inert atmosphere;
100%
With potassium carbonate In acetone Etherification;94.9%
With potassium carbonate; potassium iodide In butanone for 12h; Williamson reaction; Reflux;77.8%
With sodium methylate In methanol Heating;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-methoxycarbonylphenyl 2-tetrahydropyranyl ether
106342-09-0

4-methoxycarbonylphenyl 2-tetrahydropyranyl ether

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In acetone for 15h; Ambient temperature;100%
With pyridinium p-toluenesulfonate In acetone at 20℃;99%
With 1,5-dichloro-9,10-anthraquinone In dichloromethane for 0.5h; UV-irradiation;90%
2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate
773875-80-2

methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 2h; Inert atmosphere;
Stage #2: 2-(3-bromopropyl)isoindole-1,3-dione In dimethyl sulfoxide; mineral oil at 20℃; for 3.5h; Time; Inert atmosphere;
100%
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 3h;
Stage #2: 2-(3-bromopropyl)isoindole-1,3-dione In dimethyl sulfoxide; mineral oil at 20℃; for 70h;
89.3%
With sodium hydride 1.) DMF, 40 deg C, 1 h, 2.) DMF, 90 deg C, 5 h; Yield given. Multistep reaction;
benzyl bromide
100-39-0

benzyl bromide

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-benzyloxy-benzoic acid methyl ester
32122-11-5

4-benzyloxy-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetone at 50℃; for 1h;
Stage #2: benzyl bromide In acetone at 80℃; for 5h;
100%
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetone at 50℃; for 1h;
Stage #2: benzyl bromide In acetone at 80℃; for 5h;
100%
With potassium carbonate In acetone at 60℃;100%
1-dodecylbromide
143-15-7

1-dodecylbromide

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-(dodecyloxy)benzoate
40654-49-7

methyl 4-(dodecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetonitrile for 24h; Heating;100%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Inert atmosphere; Reflux;98%
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetonitrile at 70℃; Inert atmosphere;
Stage #2: 1-dodecylbromide In acetonitrile for 12h; Reflux; Inert atmosphere;
96%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-carbomethoxyphenyl triflate
17763-71-2

4-carbomethoxyphenyl triflate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃; for 1h;98%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 0℃;96%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

propargyl bromide
106-96-7

propargyl bromide

methyl 4-(2-propynoxy)benzoate
98260-05-0

methyl 4-(2-propynoxy)benzoate

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetone; toluene for 72h; Reflux;100%
With potassium carbonate In acetone Inert atmosphere;99%
With potassium carbonate In acetone at 65℃; for 18h; Inert atmosphere;98%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

cyanomethyl bromide
590-17-0

cyanomethyl bromide

methyl 4-(cyanomethoxy)benzoate
137988-24-0

methyl 4-(cyanomethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;100%
With potassium carbonate In acetone at 20℃;95.8%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-hydroxycyclohexanecarboxylate
3618-03-9, 6125-57-1, 17449-76-2

methyl 4-hydroxycyclohexanecarboxylate

Conditions
ConditionsYield
With hydrogen; rhodium on aluminium In ethanol under 2327.2 Torr; for 96h;100%
With hydrogen; Rh/Al2O3 In methanol under 2844.3 Torr; for 18h;98%
With hydrogen; Rh on carbon In tetrahydrofuran under 76000 Torr; for 18h;98%
1-bromo dodecane
112-29-8

1-bromo dodecane

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-decyloxybenzoate
62443-10-1

methyl 4-decyloxybenzoate

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetonitrile at 70℃; Inert atmosphere;
Stage #2: 1-bromo dodecane In acetonitrile for 12h; Reflux; Inert atmosphere;
100%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Inert atmosphere; Reflux;96%
With potassium carbonate In acetonitrile for 12h; Reflux;96%
2-(N-tert-butoxycarbonylamino)ethanol
26690-80-2

2-(N-tert-butoxycarbonylamino)ethanol

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-(2-tert-butoxycarbonylaminoethoxy)benzoic acid methyl ester
174666-16-1

4-(2-tert-butoxycarbonylaminoethoxy)benzoic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 20h; Condensation;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 5h;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 5.16h;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 17h; Cooling with ice;0.45 g
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester
89151-44-0

4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester

methyl 4-(2-N-BOC-piperidin-4-ylethoxy)benzoate
163209-93-6

methyl 4-(2-N-BOC-piperidin-4-ylethoxy)benzoate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 20h; Condensation;100%
With triphenylphosphine tagged with poly-(ethyleneglycol)-ω-monomethyl ether; diethyl azodicarboxylate tagged with poly-(ethyleneglycol)-ω-monomethyl ether In tetrahydrofuran for 20h; Mitsunobu reaction; Inert atmosphere;
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

3-(4-nitro)-benzoyl-2(3H)-benzothiazolone
187409-84-3

3-(4-nitro)-benzoyl-2(3H)-benzothiazolone

4-(4-nitro-benzoyloxy)-benzoic acid methyl ester
79859-22-6

4-(4-nitro-benzoyloxy)-benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;100%
(S)-1-bromo-3,7-dimethyloctane
3383-83-3, 59965-20-7, 72746-96-4, 79434-89-2

(S)-1-bromo-3,7-dimethyloctane

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-((S)-3,7-dimethyloctyloxy) benzoate
886761-14-4

methyl 4-((S)-3,7-dimethyloctyloxy) benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 13h;94%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 110℃; Williamson etherification;
4-(2-chloroethyl)morpholine hydrochride
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-(2-morpholinoethoxy)benzoate
92501-87-6

methyl 4-(2-morpholinoethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;100%
With caesium carbonate In acetonitrile at 80 - 85℃; for 4h; Inert atmosphere;92%
With potassium carbonate In acetone Heating;
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

isopropyl bromide
75-26-3

isopropyl bromide

methyl 4-isopropoxybenzoate
35826-59-6

methyl 4-isopropoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux;100%
With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux;100%
With potassium carbonate In acetone at 85℃; for 72h; Sealed tube;94.7%
With sodium hydride In N,N-dimethyl-formamide at 60℃;80%
chloroacetonitrile
107-14-2

chloroacetonitrile

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-(cyanomethoxy)benzoate
137988-24-0

methyl 4-(cyanomethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone at 20 - 60℃; for 88h;100%
With potassium carbonate; sodium iodide In acetone at 20 - 60℃; for 88h;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 4h;98%
1-(tert-butoxycarbonyl)-(5R)-isopropyl-(2S)-pyrrolidinylmethanol

1-(tert-butoxycarbonyl)-(5R)-isopropyl-(2S)-pyrrolidinylmethanol

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-(1-(tert-butoxycarbonyl)-(5R)-isopropyl-(2S)-pyrrolidinylmethoxy)benzoate

methyl 4-(1-(tert-butoxycarbonyl)-(5R)-isopropyl-(2S)-pyrrolidinylmethoxy)benzoate

Conditions
ConditionsYield
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran; hexane; ethyl acetate100%
4-(2-chloroethyl)morpholine hydrochride
3647-69-6

4-(2-chloroethyl)morpholine hydrochride

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-(2-morpholin-4-yl-ethoxy)-benzoic acid
134599-45-4

4-(2-morpholin-4-yl-ethoxy)-benzoic acid

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃;
Stage #2: 4-(2-chloroethyl)morpholine hydrochride In DMF (N,N-dimethyl-formamide) at 100℃; for 2h;
100%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

methyl 4-allyloxybenzoate
35750-24-4

methyl 4-allyloxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;99%
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 3-chloroprop-1-ene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
87%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;85.7%
10-bromodec-1-ene
62871-09-4

10-bromodec-1-ene

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-(dec-9-enyloxy)benzoate
117560-76-6

methyl 4-(dec-9-enyloxy)benzoate

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetonitrile at 70℃; Inert atmosphere;
Stage #2: 10-bromodec-1-ene In acetonitrile for 12h; Reflux; Inert atmosphere;
100%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

methyl 4-(but-2-yn-1-yloxy)benzoate
362705-52-0

methyl 4-(but-2-yn-1-yloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In butanone at 20℃; for 23h; Reflux;100%
With potassium carbonate In butanone at 20℃; for 23h; Reflux;100%
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide; mineral oil at 19℃; for 20h; Inert atmosphere;
79%
2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

methyl 4-((2-methoxyethoxy)methoxy)benzoate
906672-79-5

methyl 4-((2-methoxyethoxy)methoxy)benzoate

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: 2-Methoxyethoxymethyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24h;
100%
Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: 2-Methoxyethoxymethyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24h;
100%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

3,4-dichlorobenzyl bromide
18880-04-1

3,4-dichlorobenzyl bromide

4-(3,4-dichloro-benzyloxy)-benzoic acid methyl ester
84404-04-6

4-(3,4-dichloro-benzyloxy)-benzoic acid methyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 48h;100%
With potassium carbonate In acetone at 65 - 80℃; for 5h;
With potassium carbonate In acetone at 80℃; for 5h;
2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate
74808-10-9, 86520-63-0, 87119-53-7, 92052-29-4, 121238-27-5, 127061-80-7, 142831-80-9

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

4-(Methoxycarbonyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
74950-95-1

4-(Methoxycarbonyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions
ConditionsYield
Stage #1: 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate; methyl 4-hydroxylbenzoate In dichloromethane at 0℃; for 0.166667h; Molecular sieve; Inert atmosphere;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane for 3h; Molecular sieve; Inert atmosphere;
100%

99-76-3Relevant articles and documents

Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis

Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.

supporting information, (2022/02/21)

Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).

Cleavage of Carboxylic Esters by Aluminum and Iodine

Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan

, p. 4254 - 4261 (2021/03/09)

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

Guo, Baodang,Huang, Shuping,Li, Jia,Li, Min,Liu, Xuanzhong,Rao, Yijian,Wu, Yawen,Yin, Huimin,Yuan, Zhenbo,Zhang, Yan

, p. 111 - 120 (2021/06/16)

To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure–property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochemical and photophysical characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C–H and C–O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chemistry.

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