Chloroacetone → Acetonyl 4-hydroxyphenylpropionate

HRID 26038Notes

Reaction equation

HRID 26038 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21](=[O:23])[CH3:22]>CN(C)C=O.ClC(Cl)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([O:11][CH2:20][C:21]([CH3:22])=[O:23])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1025262-(4-Hydroxyphenyl)propionic acid2×

Product 1

HCID 21326463Acetonyl 4-hydroxyphenylpropionateYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 63651,1-DichloroethaneSolvent

Procedure

After 49.9 g of 4-hydroxyphenylpropionic acid was dissolved in 160 ml of dimethylformamide, 21.8 g of potassium carbonate was added to the solution at room temperature. Then 29.1 g of monochloroacetone was added dropwise to the solution at 60° C. and the reaction with 4-hydroxyphenylpropionic acid was carried out at 80°-90° C. for 1 hour. After the reaction, dimethylformamide was distilled off from the reaction solution to give a residue. After the residue was dissolved in dichloroethane, the solution was washed with water. The layer of dichloroethane was removed and the solvent was distilled off to give 64.7 g (yield 97%) of acetonyl 4-hydroxyphenylpropionate. After recrystallization from isopropylether, the product was a colorless crystalline material having a melting point of 64.5° C.

Workup

  1. distillationwas distilled off from the reaction solution
  2. customto give a residue
  3. washthe solution was washed with water
  4. customThe layer of dichloroethane was removed
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-75c5bea0e4de42d1a60057506ce3ec87
Source dataset
uspto-grants-1979_04
Patent number
US04147876

Reaction notes

Loading…