Oxalyl chloride → Butanoic acid, 4-chloro-4-oxo-, methyl ester

HRID 867403Notes

Reaction equation

HRID 867403 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-])=[O:5].C(Cl)(=O)C([Cl:13])=O>C(Cl)Cl.CN(C)C=O>[C:1]([CH2:2][CH2:3][C:4]([Cl:13])=[O:5])([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6930703Mono-Methyl Succinate

Product 1

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of mono-methyl succinate, (150 g, 1.135 mol) in 900 ml of methylene chloride and 3 ml of N,N-dimethylformamide was added 119 ml (1.26 mol) of oxalyl chloride, while keeping the pot temperature below 5° C. After the addition was complete, the reaction mixture was stirred at 0° C. for 1 hour and then concentrated to vacuo to give a crude yellow liquid, which was used without purification in the Rosenmund reduction.

Workup

  1. customthe pot temperature below 5° C
  2. additionAfter the addition
  3. concentrationconcentrated to vacuo
  4. customto give a crude yellow liquid, which
  5. customwas used without purification in the Rosenmund reduction

Sources & evidence

ORD record
ord-e42b1e4f590743a895d3abdbd89c60b4
Source dataset
uspto-grants-1988_10
Patent number
US04775662

Reaction notes

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