Methyl 4-(2-t-butoxycarbonyl-vinyl)-benzoate → Benzoic acid, 4-(2-carboxyethenyl)-, methyl ester

HRID 1180800Notes

Reaction equation

HRID 1180800 reaction equation
C([O:5][C:6]([CH:8]=[CH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)=[O:7])(C)(C)C>C(Cl)Cl.O>[C:6]([CH:8]=[CH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)([OH:7])=[O:5]

Participants

4

Reactant 1

HCID 53900295Methyl 4-(2-t-butoxycarbonyl-vinyl)-benzoate

Product 1

HCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl esterYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution at room temperature of VI (745 mg, 2.84 mmol) in CH2Cl2 (10 ml) was added trifluoroacetc acid (6 ml, 95% in water). After 27 h, the reaction mixture was concentrated, and triturated in water. After 1 h, the suspension was filtered off, rinsed with H2O, and dried to afford the title compound VII (556 mg, 2.70 mmol, 95% yield) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ(ppm): AB system (δA=8.01, δB=7.88, J=8.1 Hz, 4H), 7.68 (d, J=15.8 Hz, 1H), 6.70 (d, J=16.3 Hz, 1H), 3.90 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customtriturated in water
  3. waitAfter 1 h
  4. filtrationthe suspension was filtered off
  5. washrinsed with H2O
  6. customdried

Sources & evidence

ORD record
ord-4a7554e5bd174f49896c5710cbadaab8
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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