Phenol → Phenyl hexanoate

HRID 2398306Notes

Reaction equation

HRID 2398306 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:1]([O:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 996PhenolHCID 67340Hexanoyl chloride

Product 1

HCID 522678Phenyl hexanoateYield 94.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

30 ml (0.22 mole) of hexanoyl chloride were added dropwise over 30 minutes with stirring and cooling on an ice bath to a solution of 18.8 g (0.2 mole) of phenol in 80 ml of anhydrous pyridine and then the reaction mixture stood at room temperature for 3 hours and was poured into ice water. The mixture was extracted with ether and the ether extracts were washed with water, dilute hydrochloric acid and with water, dried over magnesium sulfate and evaporated to dryness to obtain 36.4 g of phenyl hexanoate as a yellow oil.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe ether extracts were washed with water, dilute hydrochloric acid and with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b997b201404647c483047ade54e64923
Source dataset
uspto-grants-1977_05
Patent number
US04024276

Reaction notes

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