Trifluoroacetic acid → 3-(4-Chlorobenzyl)-4-methoxy-4-oxobutanoic acid

HRID 387514Notes

Reaction equation

HRID 387514 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][CH:14]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][C:20]([OH:22])=[O:21])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687336964-Tert-butyl 1-methyl 2-(4-chlorobenzyl)succinate

Product 1

HCID 142705963-(4-Chlorobenzyl)-4-methoxy-4-oxobutanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (15 mL) was added dropwise to a solution of 4-tert-butyl 1-methyl 2-(4-chlorobenzyl)succinate (1.91 g, 6.1 mmol) in DCM (30 mL) at 0° C. The reaction mixture was then warmed to room temperature and stirred for 5 hours. The reaction was then concentrated to dryness to give 3-(4-chlorobenzyl)-4-methoxy-4-oxobutanoic acid as a syrup (1.55 g, 95%), which was used without further purification.

Workup

  1. concentrationThe reaction was then concentrated to dryness

Sources & evidence

ORD record
ord-e5b0b33562974b509bf5e16ff17d84ab
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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