Toluene → Methyl (2E)-3-(3-chlorophenyl)-2-propenoate

HRID 1662100Notes

Reaction equation

HRID 1662100 reaction equation
[Cl:1]C1C=CC=CC=1C=O.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[Cl:1][C:36]1[CH:35]=[C:34](/[CH:40]=[CH:13]/[C:12]([O:11][CH3:10])=[O:33])[CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 69962-ChlorobenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 5706327Methyl (2E)-3-(3-chlorophenyl)-2-propenoate

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chlorobenzaldehyde 7-6 (5.0 g, 35.6 mmol) in toluene (50 mL) at 25° C. was added methyl(triphenylphosphoranylidene)acetate (13.0 g, 39.1 mmol) and the reaction mixture was stirred at 110° C. for 3 h. The mixture was concentrated in vacuo and purified by normal phase silica gel chromatography (0 to 20% EtOAc in hexanes) to afford the title compound a clear oil. ESI+ MS: [M+H]+ 197.2.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by normal phase silica gel chromatography (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e299d1a957c5445fa3119f80482a0498
Source dataset
uspto-grants-2011_10
Patent number
US08030495B2

Reaction notes

Loading…