Oxalyl chloride → Propanoic acid, 3-chloro-3-oxo-, phenylmethyl ester

HRID 1373083Notes

Reaction equation

HRID 1373083 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([O-])=[O:4].C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C)C=O>[Cl:18][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22247814Benzyl malonate

Product 1

HCID 11148560Propanoic acid, 3-chloro-3-oxo-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of commercially available mono-benzyl malonate (Aldrich Chemical Co., Milwaukee, Wis.) (7.76 g, 40 mmol) in methylene chloride (100 mL) was added oxalyl chloride (14 mL, 160 mmol) followed by 3 drops of dimethylformamide. The reaction mixture was stirred at room temperature for 3 hours and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21f3ae4211d7424dbaef6620a4d69e7f
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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