Chloroacetic Acid → (2-Phenylethoxy)acetic acid

HRID 2100466Notes

Reaction equation

HRID 2100466 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:13][C:14]([OH:16])=[O:15]>CN(C=O)C>[CH2:10]([O:11][CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 60542-PhenylethanolHCID 24758Sodium hydride

Product 1

HCID 13208922(2-Phenylethoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (6.87 g, 172 mmol) was added slowly to a solution of 2-phenylethanol ([60-12-8], 6.00 g, 5.88 ml, 49.1 mmol) in DMF (50 ml). The reaction mixture was heated and kept for 10 min at 60° C. Chloroacetic acid ([79-11-8], 8.12 g, 86 mmol) was added slowly and carefully (exothermic), and the mixture was kept for 1 h at 60° C. The mixture was poured on ice and extracted twice with diethyl ether. Then the water phase was acidified (HCl, pH˜3) and extracted twice with ethyl acetate. Phenethyloxy-acetic acid [81228-03-7] was obtained after drying (Na2SO4), and evaporation of the solvent. The compound was sufficiently pure for the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. waitcarefully (exothermic), and the mixture was kept for 1 h at 60° C
  3. additionThe mixture was poured on ice
  4. extractionextracted twice with diethyl ether
  5. extractionextracted twice with ethyl acetate

Sources & evidence

ORD record
ord-c256d2f4d59f47debb4ff954785466ea
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

Loading…