306-08-1

Basic information

• Product Name: Homovanillic acid
• Synonyms: 4-Hydroxy-3-methoxybenzeneacetic acid;4-hydroxy-3-methoxy-benzeneaceticaci;4-hydroxy-3-methoxy-Benzeneaceticacid;Acetic acid, (4-hydroxy-3-methoxyphenyl)-;Homovanilic acid;Homovanillinic acid;Vanilacetic acid;Vanillacetic Acid
• CAS NO: 306-08-1
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• EINECS: 206-176-7
• Product Categories: Pharmaceutical Intermediates;Multisubstituted Benzene;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 306-08-1.mol
• Article Data: 23

Chemical Properties

• Melting Point: 142-145 °C(lit.)
• Boiling Point: 235.56°C (rough estimate)
• Flash Point: 151.9 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.1634 (rough estimate)
• Vapor Pressure: 4.36E-06mmHg at 25°C
• Refractive Index: 1.4209 (estimate)
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 4.39±0.10(Predicted)
• Water Solubility: soluble
• Stability: Hygroscopic
• Merck: 14,4740
• BRN: 2213447
• CAS DataBase Reference: Homovanillic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Homovanillic acid(306-08-1)
• EPA Substance Registry System: Homovanillic acid(306-08-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 306-08-1(Hazardous Substances Data)

Usage

Description

Homovanillic acid (HVA) is a dopamine metabolite. It is formed via deamination of dopamine by monoamine oxidase (MAO) to produce 3,4-dihydroxyphenylacetic acid (DOPAC; ) followed by DOPAC metabolism by catechol-O-methyltransferase (COMT). HVA undergoes hydrogen peroxide-dependent oxidation in the presence of horseradish peroxidase to form a fluorescent dimer that displays excitation/emission maxima of 312/420 nm, respectively. It has been used to quantify hydrogen peroxide production in macrophages and neutrophils.

Chemical Properties

white to beige crystalline powder

Uses

Different sources of media describe the Uses of 306-08-1 differently. You can refer to the following data:
1. A neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite.
2. Fluorimetric reagent and major catecholamine metaboliteHomovanillic acid is used as a reagent in the determination of oxidative enzymes. It is associated with dopamine levels in the brain. Its presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

Definition

ChEBI: A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.

Biological Activity

Fluorimetric reagent and major catecholamine metabolite. Used for fluorimetric determination of oxidative enzymes including glucose oxidase.

InChI:InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)/p-1

Synthetic route

4-hydroxy-3-methoxyphenylacetonitrile (4468-59-1) → Homovanillic acid (306-08-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 80℃; for 48h; Inert atmosphere;	89%
With potassium hydroxide In ethanol Heating;	74%
With sodium hydroxide In 2-methoxy-ethanol

4-hydroxy-3-methoxy-mandelic acid (55-10-7) → Homovanillic acid (306-08-1)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water at 80℃; for 4h;	88%
	75%
With 5%-palladium/activated carbon; hydrogen; acetic acid In water

3-methoxy-4-hydroxy mandelic acid (13244-77-4) → Homovanillic acid (306-08-1)

Conditions	Yield
With formic acid; phosphoric acid; sodium hydrogensulfite In water at 100℃; under 3750.3 Torr; for 9h;	71%

4-Acetoxy-3-methoxyphenylacetaldehyde (6391-59-9) → Homovanillic acid (306-08-1) + 2-(4-acetoxy-3-methoxyphenyl)acetic acid (5447-38-1)

Conditions	Yield
With potassium permanganate; magnesium sulfate; acetone

4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one (60470-82-8, 39600-31-2) → Homovanillic acid (306-08-1)

Conditions	Yield
With sodium hydroxide anschliessend Behandeln mit wss. H2O2;

2-(4-acetoxy-3-methoxyphenyl)acetic acid (5447-38-1) → Homovanillic acid (306-08-1)

Conditions	Yield
With sodium hydroxide

m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone (18692-68-7, 71413-82-6, 74857-79-7) + furan-2,3,5(4H)-trione pyridine (1:1) → Homovanillic acid (306-08-1)

Conditions	Yield
folgend Behandeln mit Wasserstoffperoxyd in Eisessig;

(4-acetoxy-3-methoxy-phenyl)-acetonitrile (5438-51-7) → Homovanillic acid (306-08-1)

Conditions	Yield
With potassium hydroxide

1-benzoyloxy-4-chloromethyl-2-methoxy-benzene (873376-14-8) → Homovanillic acid (306-08-1)

Conditions	Yield
With potassium cyanide anschliessend Erhitzen mit wss. Natronlauge;

[6]-shogaol (23513-13-5, 104186-09-6, 555-66-8) → Homovanillic acid (306-08-1) + 5-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-dihydro-furan-2-one

Conditions	Yield
for 168h; biotransformation by aspergillus niger;	A 60 mg B 36 mg

4-benzyloxy-3-methoxyphenylacetic acid (29973-91-9) → Homovanillic acid (306-08-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

trans-coniferyl aldehyde (458-36-6) → methoxyhydroquinone (824-46-4) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) + Homovanillic acid (306-08-1) + vanillin (121-33-5)

Conditions	Yield
With peracetic acid In ethanol for 1h; pH=7; Product distribution; Further Variations:; Reagents; Oxidation;	A 10.1 % Chromat. B 13.6 % Chromat. C 10.9 % Chromat. D 7.1 % Chromat.

4-Acetoxy-3-methoxyphenylacetaldehyde (6391-59-9) + magnesium sulfate (7487-88-9) + acetone (67-64-1) + KMnO4 → Homovanillic acid (306-08-1) + 2-(4-acetoxy-3-methoxyphenyl)acetic acid (5447-38-1)

azlactone of/the/ 3-methoxy-4-acetoxy-α-benzamino-cinnamic acid → Homovanillic acid (306-08-1)

Conditions	Yield
With sodium hydroxide man gibt zu der Loesung erst Eisessig und dann H2O2;

(3-methoxy-4-oxo-cyclohexa-2,5-dienyliden)-acetonitrile (91054-36-3) + hydrogen iodide (10034-85-2) → Homovanillic acid (306-08-1) + 2,3-bis-(4-hydroxy-3-methoxy-phenyl)-succinonitrile

Conditions	Yield
5-min. Erhitzen;

4-amino-butyric acid 2-(4-hydroxy-3-methoxy-phenyl)-2-oxo-ethyl ester (284043-11-4) → Homovanillic acid (306-08-1) + 2,4'-dihydroxy-3'-methoxyacetophenone (18256-48-9) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With water Hydrolysis; reduction; rearrangement; UV-irradiation;

γ-O-(4-hydroxy-3-methoxyphenacetyl) L-glutamate, trifuoroacetate salt → L-glutamic acid (56-86-0) + Homovanillic acid (306-08-1) + 2,4'-dihydroxy-3'-methoxyacetophenone (18256-48-9) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2)

Conditions	Yield
With water Hydrolysis; rearrangement; reduction; UV-irradiation;

4-hydroxymethyl-2-methoxyphenol (498-00-0) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / dimethylformamide / 20 h / 130 °C 2: 74 percent / KOH / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / ethanol; water / 48 h / 80 °C / Inert atmosphere View Scheme

α-bromo-3-methoxy-4-hydroxyacetophenone (69638-06-8) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: DBU / dioxane / 12 h / 0 - 20 °C 2: TFA / 4 h / 0 °C 3: H2O / UV-irradiation View Scheme
Multi-step reaction with 3 steps 1: 57 percent / DBU / benzene / 12 h / 20 °C 2: 95.3 percent / TFA / 4 h / 0 °C 3: H2O / UV-irradiation View Scheme

1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 47 percent / cupric bromide / CHCl3; ethyl acetate / 4 h / 20 °C 2: DBU / dioxane / 12 h / 0 - 20 °C 3: TFA / 4 h / 0 °C 4: H2O / UV-irradiation View Scheme
Multi-step reaction with 4 steps 1: 47 percent / cupric bromide / CHCl3; ethyl acetate / 4 h / 20 °C 2: 57 percent / DBU / benzene / 12 h / 20 °C 3: 95.3 percent / TFA / 4 h / 0 °C 4: H2O / UV-irradiation View Scheme

2-(4-hydroxy-3-methoxyphenyl)-2-oxoethyl-4-[(tert-butoxycarbonyl)amino]butanoate (284043-13-6) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: TFA / 4 h / 0 °C 2: H2O / UV-irradiation View Scheme

γ-O-(4-hydroxy-3-methoxyphenacetyl) t-butyl N-t-boc L-glutamate (284043-05-6) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95.3 percent / TFA / 4 h / 0 °C 2: H2O / UV-irradiation View Scheme

methyl 4-benzyloxy-3-methoxyphenylethanoate (16209-54-4) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 10percent KOH / methanol; H2O 2: H2 / 10percent Pd-C / aq. ethanol View Scheme

4-(hydroxymethyl)-2-methoxyphenyl benzoate (174840-51-8) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium chloride; thionyl chloride 2: aqueous potassium cyanide / anschliessend Erhitzen mit wss. Natronlauge View Scheme

eugenol acetate (93-28-7) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate; ozone / und anschliesende Hydrierung an Palladium/Kohle 2: potassium permanganate; magnesium sulfate; aqueous acetone View Scheme
Multi-step reaction with 2 steps 1: KMnO4; water 2: NaOH-solution View Scheme

4-allylguaiacol (97-53-0) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 3 steps 2: KMnO4; water 3: NaOH-solution View Scheme

2-methoxy-4-((methylamino)methyl)phenol (42973-53-5) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: aq. NaOH / 2-methoxy-ethanol View Scheme

vanillin (121-33-5) → Homovanillic acid (306-08-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) EtOH, (ii) H2, PtO2 2: dimethylformamide 3: aq. NaOH / 2-methoxy-ethanol View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 24.5 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere 3: sodium hydroxide / ethanol; water / 48 h / 80 °C / Inert atmosphere View Scheme

8-O-4′-diferulic acid (215872-63-2) → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 3-(3-hydroxyphenyl)-propanoic acid (621-54-5) + 3-(4-hydroxy-3-methoxyphenyl)propionic acid (1135-23-5) + caffeic acid (331-39-5) + 3,4-dihydroxyphenylacetate (102-32-9) + Homovanillic acid (306-08-1) + dihydrocaffeic acid (1078-61-1) + danshensu (23028-17-3) + 3-(4-hydroxy-3-methoxyphenyl)lactic acid (2475-56-1) + 3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid (1081-71-6)

Conditions	Yield
With D-glucose In dimethyl sulfoxide at 37℃; aq. buffer; anaerobic atmosphere; Enzymatic reaction;

...Expand

methanol (67-56-1) + Homovanillic acid (306-08-1) → 2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester (15964-80-4)

Conditions	Yield
With sulfuric acid for 3h; Reflux;	100%
With toluene-4-sulfonic acid
With sulfuric acid at 20℃; for 4h; Reflux;

Homovanillic acid (306-08-1) + isopropyl bromide (75-26-3) → isopropyl 2-(4-isopropoxy-3-methoxyphenyl)acetate (1256581-67-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere;	100%

Homovanillic acid (306-08-1) + recorcinol (108-46-3) → 1-(2,4-dihydroxyphenyl)-2-(4'-hydroxy-3'-methoxyphenyl)ethanone (40456-49-3)

Conditions	Yield
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;	99%
With bis(trifluoromethanesulfonyl)amide In various solvent(s) at 90℃; for 0.0666667h; Friedel-Crafts reaction; microwave irradiation;	70%
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Friedel-Crafts reaction;	57%

ethanol (64-17-5) + Homovanillic acid (306-08-1) → ethyl homovanillate (60563-13-5)

Conditions	Yield
With sulfuric acid for 2h; Reflux;	99%
With sulfuric acid	99%
With sulfuric acid for 2h; Reflux;	80%
With sulfuric acid Reflux;
With sulfuric acid at 90℃; for 7h;

Homovanillic acid (306-08-1) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethyl 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acetate (78324-15-9)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;	98%
With 1H-imidazole In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;	64%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;

Homovanillic acid (306-08-1) → 2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid (2989-10-8)

Conditions	Yield
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7;	98%

Homovanillic acid (306-08-1) + acetic anhydride (108-24-7) → 2-(4-acetoxy-3-methoxyphenyl)acetic acid (5447-38-1)

Conditions	Yield
With sulfuric acid	97%
With sulfuric acid Ambient temperature;	79%

2-(methylamino)-1-phenylethanol (68579-60-2) + Homovanillic acid (306-08-1) → 2-(4-hydroxy-3-methoxy-phenyl)-N-(2-hydroxy-2-phenyl-ethyl)-N-methyl-acetamide (749247-36-7)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	97%

4-Methylbenzyl alcohol (589-18-4) + Homovanillic acid (306-08-1) → 1-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)propan-2-one

Conditions	Yield
Stage #1: 4-Methylbenzyl alcohol; Homovanillic acid With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 55℃; for 4h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 2h; Temperature; Inert atmosphere; Cooling with ice;	96.8%

Homovanillic acid (306-08-1) + benzyl bromide (100-39-0) → benzyl 2-(4-(benzyloxy)-3-methoxyphenyl)acetate (65340-85-4)

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Reflux;	95%
With potassium carbonate In acetonitrile at 80℃; for 8h;	88%
With sodium In methanol

trifluoromethylsulfonic anhydride (358-23-6) + Homovanillic acid (306-08-1) → 2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid (1243245-99-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	95%

Homovanillic acid (306-08-1) + 4-Methoxyphenethylamine (55-81-2) → 2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide (1395084-66-8)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux; Inert atmosphere;	95%

Homovanillic acid (306-08-1) + N-(benzyloxy)octan-1-amine (122149-21-7) → N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide (1400943-51-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4.5h; Inert atmosphere;	94%

Homovanillic acid (306-08-1) + O-benzyl-N-heptylhydroxylamine (112151-61-8) → N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide (1400943-49-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	93%

Homovanillic acid (306-08-1) + Phenyl-acetic acid (1aR,1bS,4aS,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester (850163-67-6) → 13-acetyl-20-homovanillyl-12-phenylacetyl-4α-phorbol (777859-96-8)

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;	91%

Å molecular sieve + Homovanillic acid (306-08-1) + 3-(3,4-dimethylphenyl)propylamine (142332-70-5) → KR-25003 (142333-36-6)

Conditions	Yield
In dichloromethane	90%

Homovanillic acid (306-08-1) + 3-(3,4-dimethylphenyl)propylamine (142332-70-5) → KR-25003 (142333-36-6)

Conditions	Yield
molecular sieve In dichloromethane	90%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h;

Homovanillic acid (306-08-1) + benzylamine (100-46-9) → N-benzyl-4-hydroxy-3-methoxyphenylacetamide (391609-30-6)

Conditions	Yield
With 4 A molecular sieve at 140 - 150℃; for 3h;	89%

Homovanillic acid (306-08-1) + 3-iodobenzylamine hydrochloride (3718-88-5) → 2-(4-hydroxy-3-methoxyphenyl)-N-(3-iodobenzyl)acetamide (873099-30-0)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	88%

Homovanillic acid (306-08-1) + 2-(3-methoxyphenyl)-1-ethanamine (2039-67-0) → 2-(4-hydroxy-3-methoxyphenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 4h;	88%

methanol (67-56-1) + Homovanillic acid (306-08-1) + trimethyl orthoformate (149-73-5) → 2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester (15964-80-4)

Conditions	Yield
With sulfuric acid for 18h; Heating / reflux;	85%

3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indole (844901-56-0) + Homovanillic acid (306-08-1) → 4-(2-{3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl}-2-oxoethyl)-2-methoxyphenol (847064-35-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 0 - 20℃;	82%

8-methyl-1-nonanol (55505-26-5) + Homovanillic acid (306-08-1) → 8-methylnonyl homovanillate (951221-76-4)

Conditions	Yield
With magnesium sulfate; novozyme 435 In toluene at 50℃; for 16h; Enzymatic reaction;	81.5%

Homovanillic acid (306-08-1) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-hydroxy-4-methoxyphenyl)acetamide (361389-65-3)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	79%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	79%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;

propan-1-ol (71-23-8) + Homovanillic acid (306-08-1) → Propyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (52744-26-0)

Conditions	Yield
With acetyl chloride at 60℃; for 3h;	78.2%
With sulfuric acid at 90℃; for 7h;

2-phenylethanol (60-12-8) + Homovanillic acid (306-08-1) → 2-phenylethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Conditions	Yield
With di-isopropyl azodicarboxylate; thiamine diphosphate In tetrahydrofuran at 20℃; Mitsunobu esterification;	78%

2-Phenoxyethanol (122-99-6) + Homovanillic acid (306-08-1) → 2-phenoxyethyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Conditions	Yield
With sulfuric acid In toluene for 2h; Dean-Stark; Reflux;	77.3%

piperidine (110-89-4) + Homovanillic acid (306-08-1) → 2-(4-Hydroxy-3-methoxy-phenyl)-1-piperidin-1-yl-ethanone (53283-49-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	75%

Upstream product

• 6391-59-9 4-Acetoxy-3-methoxyphenylacetaldehyde 
• 5447-38-1 2-(4-acetoxy-3-methoxyphenyl)acetic acid 
• 29973-91-9 4-benzyloxy-3-methoxyphenylacetic acid 
• 13244-77-4 3-methoxy-4-hydroxy mandelic acid 
• 7487-88-9 magnesium sulfate 
• 67-64-1 acetone 
• 91054-36-3 (3-methoxy-4-oxo-cyclohexa-2,5-dienyliden)-acetonitrile 
• 10034-85-2 hydrogen iodide 
• 97-53-0 4-allylguaiacol 
• 215872-63-2 8-O-4'-dehydrodiferulic acid 
• 9005-53-2 lignin 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 485-80-3 S-adenosyl-L-methionine 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 

Downstream Products

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 110879-32-8 4-carbethoxy-3-methoxyphenylethanoic acid 
• 131656-82-1 ((4-hydroxy-3-methoxyphenyl)acetyl)pyrrolidine 
• 37148-61-1 Trimethylsilylderivat von Homovanillinsaeure 
• 74-87-3 methylene chloride 
• 391609-30-6 N-benzyl-4-hydroxy-3-methoxyphenylacetamide 
• 749247-36-7 2-(4-hydroxy-3-methoxy-phenyl)-N-(2-hydroxy-2-phenyl-ethyl)-N-methyl-acetamide 
• 873099-30-0 2-(4-hydroxy-3-methoxyphenyl)-N-(3-iodobenzyl)acetamide 
• 289903-64-6 homovanillic acid pentafluorophenyl ester 
• 765302-59-8 2-(3-FORMYL-4-HYDROXY-5-METHOXYPHENYL)ACETIC ACID 
• 776324-87-9 [4-(difluoromethoxy)-3-methoxyphenyl]acetic acid 
• 850312-67-3 C₁₆H₁₅NO₇ 
• 847064-35-1 4-(2-{3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl}-2-oxoethyl)-2-methoxyphenol 

Relevant articles and documents

Design, synthesis, and evaluation of phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents

In this paper, we designed and synthesized a series of novel phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents. The best compound 10 had relatively high affinity for the GABAA receptor and low affinity for thirteen other off-target receptors. In three animal models (mice, rats, and rabbits), compound 10 exerted potent hypnotic effects (HD50 = 5.2 mg/kg in rabbits), comparable duration of the loss of righting reflex (LORR), and significant shorter recovery time (time to walk) than propanidid. Furthermore, compound 10 (TI = 18.1) showed higher safety profile than propanidid (TI = 14.7) in rabbits. Above results suggested that compound 10 may have predictable and rapid recovery profile in anesthesia.

Phenylacetic acid ester compound and use thereof

The invention relates to a phenylacetate compound as shown in a general formula (I) and a pharmaceutical composition containing the phenylacetate compound, as well as application in anesthesia and sedation.

Electrochemical Lignin Degradation in Ionic Liquids on Ternary Mixed Metal Electrodes

Lignin is the second most abundant natural polymer and a promissing feedstock for the generation of renewable aromatic chemicals. We present an fundamental approach for the electrocatalytic cleavage of lignin dissolved in a recoverable, inexpensive ionic liquid using mixed metal oxide electrodes of different compositions. The distribution of depolymerization products generated by electrochemical oxidation were analyzed by means of mass spectrometry. The distribution and yield of the cracked species was found to depended strongly on the implemented metal catalyst and therefore offers the potential to tailor the amount and composition of the low molecular weight cleavage products. This approach could help to provide a more sustainable valorization of lignin for the potential production of high value aromatic compounds due to synergistic effects.