Acetic acid, 2-chloro-, phenylmethyl ester → HCID 19387447, compound

HRID 1757305Notes

Reaction equation

HRID 1757305 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1(C)C=CC=CC=1>[Cl-:20].[C:14]1([P+:7]([CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 11776Triphenylphosphine

Product 1

HCID 19387447HCID 19387447, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

23.6 g (0.1 mol) of triphenylphosphine were suspended in 70 ml of toluene. 18.5 g (0.1 mol) of benzyl chloroacetate were added dropwise and the mixture was heated at the boil for two hours. After cooling down to room temperature, the precipitated product was filtered off and washed with diethyl ether. Drying left 40.8 g (corresponding to a yield of 90%) of the title compound in the form of colorless crystals. The product was more than 99% pure.

Workup

  1. temperaturethe mixture was heated at the boil for two hours
  2. filtrationthe precipitated product was filtered off
  3. washwashed with diethyl ether
  4. customDrying
  5. waitleft 40.8 g (corresponding to a yield of 90%) of the title compound in the form of colorless crystals

Sources & evidence

ORD record
ord-51dc52e2305f48e8a5b792fe0d9684ee
Source dataset
uspto-grants-1995_08
Patent number
US05445724

Reaction notes

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