(E)-tert-butyl 3-(2-acetyl-5-chlorophenyl)acrylate → (E)-3-(2-acetyl-5-chlorophenyl)acrylic acid

HRID 515758Notes

Reaction equation

HRID 515758 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]([O:15]C(C)(C)C)=[O:14])(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 89499883(E)-tert-butyl 3-(2-acetyl-5-chlorophenyl)acrylate

Product 1

HCID 66744692(E)-3-(2-acetyl-5-chlorophenyl)acrylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of Intermediate 4A (0.048 g, 0.171 mmol) in 50% TFA/DCM (2 mL) was stirred at rt. After 1 h, the reaction was concentrated to give Intermediate 4 (0.038 g, 100% yield) as a yellow solid. The material was carried onto the next step without further purification. MS (ESI) m/z: 225.1 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-e4330052f8d647b2a0412124937ab8eb
Source dataset
uspto-grants-2015_08
Patent number
US09108951B2

Reaction notes

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