1083-27-8

Basic information

• Product Name: HEXYL 4-HYDROXYBENZOATE
• Synonyms: HEXYL 4-HYDROXYBENZOATE;HEXYLPARABEN;4-HYDROXYBENZOIC ACID HEXYL ESTER;4-HYDROXYBENZOIC ACID N-HEXYL ESTER;N-HEXYL P-HYDROXYBENZOATE;4-hydroxy-benzoicacihexylester;hexylp-hydroxybenzoate;p-hydroxybenzoicacidhexylester
• CAS NO: 1083-27-8
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28
• Product Categories: Aromatic Esters
• Mol File: 1083-27-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 53°C
• Boiling Point: 171°C/2mmHg(lit.)
• Flash Point: 138.5°C
• Appearance: /
• Density: 1.0850 (rough estimate)
• Vapor Pressure: 4.83E-05mmHg at 25°C
• Refractive Index: 1.4940 (estimate)
• Solubility: soluble in Methanol
• PKA: 8.24±0.15(Predicted)
• Water Solubility: 137.6mg/L(25 oC)
• CAS DataBase Reference: HEXYL 4-HYDROXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXYL 4-HYDROXYBENZOATE(1083-27-8)
• EPA Substance Registry System: HEXYL 4-HYDROXYBENZOATE(1083-27-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: DH2204000
• Hazardous Substances Data: 1083-27-8(Hazardous Substances Data)

Usage

Uses

Hexyl 4-Hydroxybenzoate is used in preparation method of Propranolol Hydrochloride cubic liquid crystal gel.

InChI:InChI=1/C13H18O3/c1-2-3-4-5-10-16-13(15)11-6-8-12(14)9-7-11/h6-9,14H,2-5,10H2,1H3

Synthetic route

4-Hydroxyacetophenone (99-93-4) + hexan-1-ol (111-27-3) → hexyl paraben (1083-27-8)

Conditions	Yield
With iron(III) chloride; ammonium persulfate In tetrachloromethane; 1,2-dichloro-ethane at 120℃; for 15h;	76%

4-hydroxy-benzaldehyde (123-08-0) + 1-(tert-butyldimethylsilyl)oxyhexane (80033-60-9) → hexyl paraben (1083-27-8)

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; Selectfluor In acetonitrile at 20℃; for 7h; Inert atmosphere; Irradiation;	73%

hexan-1-ol (111-27-3) + 4-hydroxy-benzoic acid (99-96-7) → hexyl paraben (1083-27-8)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;	66%
With sulfuric acid In toluene for 4h; Heating;	53.2%
With hydrogenchloride at 150℃;

(E)-1,3-diethyl-2-(hexyltriaz-2-en-1-ylidene)-2,3-dihydro-1H-imidazole + 4-hydroxy-benzoic acid (99-96-7) → n-hexyl 4-(hexyloxy)benzoate (111222-69-6) + hexyl paraben (1083-27-8) + C7H13N3

Conditions	Yield
In methanol; dichloromethane at 20℃; for 4h; Inert atmosphere;	A 12% B 51% C n/a

1-bromo-hexane (111-25-1) + 4-hydroxy-benzoic acid (99-96-7) → para-hexyloxybenzoic acid (1142-39-8) + hexyl paraben (1083-27-8)

Conditions	Yield
With PEG 200; potassium hydroxide at 80℃; for 2h; Title compound not separated from byproducts;	A 83 % Spectr. B 7 % Spectr.
With PEG 200; potassium hydroxide In 1,4-dioxane at 80℃; for 2h; Title compound not separated from byproducts;	A 73 % Spectr. B 11 % Spectr.

1-bromo-hexane (111-25-1) → hexyl paraben (1083-27-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch 6-taegiges Kochen 2: hydrogen chloride / 150 °C View Scheme
Multi-step reaction with 2 steps 2: hydrogen chloride / 150 °C View Scheme

1,2,4-tris(4-chloroformylphenyloxycarbonyl)benzene + hexyl paraben (1083-27-8) → C69H66O18 (1194090-79-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;	88%
With triethylamine In dichloromethane at 20℃; for 5h;

hexyl paraben (1083-27-8) → hexyl 4-[(aminosulphonyl)oxy]benzoate

Conditions	Yield
With sulphamoyl chloride; sodium hydride In N,N-dimethyl-formamide; toluene for 10h; Heating;	35.4%
Stage #1: hexyl paraben With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene
Stage #1: hexyl paraben With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene for 10h;

hexyl paraben (1083-27-8) → phosphoric acid tris-(4-hexyloxycarbonyl-phenyl ester)

Conditions	Yield
With trichlorophosphate

hexyl paraben (1083-27-8) + 2-(diethylamino)ethyl chloride (100-35-6) → 4-(2-diethylamino-ethoxy)-benzoic acid hexyl ester

4-iodobenzoic acid (619-58-9) + hexyl paraben (1083-27-8) → 4-(n-Hexyloxycarbonyl)phenyl 4'-iodobenzoate

Conditions	Yield
With dicyclohexyl-carbodiimide; 4-pyrrolidin-1-ylpyridine In diethyl ether Ambient temperature;

hexyl paraben (1083-27-8) + benzyl chloride (100-44-7) → p-Benzyloxybenzoesaeure-n-hexylester (56441-76-0)

Conditions	Yield
With sodium ethanolate

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol (678-39-7) + hexyl paraben (1083-27-8) → 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-benzoic acid hexyl ester

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5, 42996-84-9) + hexyl paraben (1083-27-8) → 4-[(E)-3-(4-Methoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-p-ethoxycinnamoyl chloride (77251-75-3) → 4-[(E)-3-(4-Ethoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + (E)-4-propoxycinnamic acid chloride (77251-76-4) → 4-[(E)-3-(4-Propoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + (E)-4-butoxycinnamic acid chloride (77251-77-5) → 4-[(E)-3-(4-Butoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-p-pentyloxycinnamoyl chloride (77251-78-6) → 4-[(E)-3-(4-Pentyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-hexyloxycinnamoyl chloride (77251-79-7) → 4-[(E)-3-(4-Hexyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-p-heptyloxycinnamoyl chloride (77251-80-0) → 4-[(E)-3-(4-Heptyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-octyloxycinnamoyl chloride (77251-81-1) → 4-[(E)-3-(4-Octyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + trans-decyloxycinnamoyl chloride (77251-82-2) → 4-[(E)-3-(4-Decyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + 4-dodecyloxycinnamoyl chloride (77251-83-3) → 4-[(E)-3-(4-Dodecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + 4-n-tetradecyloxycinnamoyl chloride (130286-00-9) → 4-[(E)-3-(4-Tetradecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + 4-hexadecyloxycinnamoyl chloride (77251-84-4) → 4-[(E)-3-(4-Hexadecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester

Conditions	Yield
With pyridine for 0.166667h;

hexyl paraben (1083-27-8) + 1,3-phenylene bis(methyliminobenzoic acid) → C48H48N2O8

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

hexyl paraben (1083-27-8) → 4'-(n-Hexyloxycarbonyl)phenyl 4''-<(4-(S)-2'-methylbutoxy-2,3,5,6-tetrafluorophenyl)ethynyl>benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: DCC / 4-pyrrolidinopyridine / diethyl ether / Ambient temperature 2: Et3N / bis(triphenylphosphine)palladium dichloride, copper(I) iodide / Heating View Scheme

sulphur dichloride + zinc chloride anhydrate + hexyl paraben (1083-27-8) → 3,3'-thiobis(hexyl p-hydroxybenzoate) (107490-77-7)

Conditions	Yield
In chloroform

hexyl paraben (1083-27-8) + 4,5-dichlorophthalonitrile (139152-08-2) → 4,5-bis[(4-hexyloxycarbonyl)phenoxy]phthalonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h;	2.2 g

Upstream product

• 111-27-3 hexan-1-ol 
• 99-96-7 4-hydroxy-benzoic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 80033-60-9 tert-butyldimethyl(n-hexyloxy)silane 
• 111-25-1 1-bromo-hexane 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 107490-77-7 3,3'-thiobis(hexyl p-hydroxybenzoate) 
• 56441-76-0 p-Benzyloxybenzoesaeure-n-hexylester 
• 1194090-79-3 C₆₉H₆₆O₁₈ 

Relevant articles and documents

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METHOD FOR PRODUCING HEXYL 4-HYDROXYBENZOATE

PROBLEM TO BE SOLVED: To provide a production method that makes it possible to obtain hexyl 4-hydroxybenzoate with excellent productivity, reduced by-products, and high yield, and a production method that makes it possible to obtain high-purity hexyl 4-hydroxybenzoate. SOLUTION: The present invention provides a method for producing hexyl 4-hydroxybenzoate represented by formula (1), including the step of making a reaction occur between hexyl 4-hydroxybenzoate of 1 molar equivalent and 1-hexanol of 0.8-3.0 molar equivalents in the presence of an acid catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT