1-(Phenylmethyl) butanedioate → Benzyl 4-chloro-4-oxobutanoate

HRID 444594Notes

Reaction equation

HRID 444594 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:19])=O>C1C=CC=CC=1>[Cl:19][C:12]([CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])=[O:13]

Participants

4

Reactant 2

HCID 87881-(Phenylmethyl) butanedioateHCID 65578Oxalyl chloride

Product 1

HCID 12550027Benzyl 4-chloro-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5 g of succinic acid monobenzyl ester in 60 ml of benzene was added 11 ml of oxalyl chloride. After 5 hrs at 20° C., gas evolution ceased and the solvent and excess oxalyl chloride was evaporated at 20° C. The residue was held at 1 torr for 1 hr to yield 5.19 g of crude benzyl 3-chloroformylpropionate; ir 1788 and 1735 cm-1.

Workup

  1. customthe solvent and excess oxalyl chloride was evaporated at 20° C
  2. waitThe residue was held at 1 torr for 1 hr

Sources & evidence

ORD record
ord-13d2835e4bcc46158f505404a5d34506
Source dataset
uspto-grants-1981_04
Patent number
US04264765

Reaction notes

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