Diazomethane → Methyl 5-chloro-4-oxopentanoate

HRID 1391850Notes

Reaction equation

HRID 1391850 reaction equation
[N+](=[CH2:3])=[N-].[Cl-:4].[CH2:5]([O:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=O)C>>[CH3:5][O:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([CH2:3][Cl:4])=[O:13]

Participants

3

Reactant 2

HCID 9550DiazomethaneHCID 77519041Succinic acid monoethyl ester monochloride

Product 1

HCID 11789557Methyl 5-chloro-4-oxopentanoate

Procedure

In EP 58392 a procedure for the production of 5-chlorolevulinic acid ethyl ester is described that starts from succinic acid mono ethyl ester mono chloride. This compound is converted with diazo methane at −5° C. and is after that worked up by passing in hydrogen chloride. You receive so the desired compound in pure form and in a high yield but the difficult handling of explosive diazo methane makes this method for the large-scale use not suitable. The same procedure is described in PL 136454. Instead of the succinic acid mono ethyl ester mono chloride the respective methyl ester derivative is used and results in the formation of 5-chlorolevulinic acid methyl ester.

Workup

  1. customin a high yield

Sources & evidence

ORD record
ord-5b8daecae1b640bcb6a1484cd4f1d95a
Source dataset
uspto-grants-2008_03
Patent number
US07339073B2

Reaction notes

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