t-Butyl 4-phenyl-2-butenoate → 4-Phenyl-2-butenoic acid

HRID 1107112Notes

Reaction equation

HRID 1107112 reaction equation
[C:1]1([CH2:7][CH:8]=[CH:9][C:10]([O:12]C(C)(C)C)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.FC(F)(F)C(O)=O>[C:1]1([CH2:7][CH:8]=[CH:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 53401901t-Butyl 4-phenyl-2-butenoate

Product 1

HCID 534018584-Phenyl-2-butenoic acidYield 99.85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6.3 g (28.86 mmol) of t-butyl 4-phenylbut-2-enoate in 100 mL of CH2Cl2 and 30 mL of trifluoroacetic acid is stirred at 25° C. for 18 hours. The reaction is concentrated in vacuo to afford 4.67 g (99.85%) of 4-phenylbut-2-enoic acid as a yellow crystalline solid.

Workup

  1. concentrationThe reaction is concentrated in vacuo

Sources & evidence

ORD record
ord-6bf6f2351585416a8bfcb7d53d6549df
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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