Methanol → (E)-Methyl 3-(3-chloro-2-methylphenyl)acrylate

HRID 2175311Notes

Reaction equation

HRID 2175311 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:18][C:19]([O-:21])=[O:20])C=CC=CC=1.[CH3:34]O>>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4](/[CH:5]=[CH:18]/[C:19]([O:21][CH3:34])=[O:20])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 131626623-Chloro-2-methylbenzaldehydeHCID 218948102-(Triphenylphosphoranylidene)acetate

Product 1

HCID 86712608(E)-Methyl 3-(3-chloro-2-methylphenyl)acrylateYield 24%

Procedure

A mixture of (2-methoxy-2-oxoethyl)triphenylphosphonium bromide (10.0 g, 24.08 mmol) in 100 mL DCM, 50 mL water and NaOH (10 N) (4.82 ml, 48.2 mmol) was vigorously shaken in a separatory funnel. The organic layer was separated and the aqueous phase was extracted with DCM. The combined organic layers were dried (MgSO4) and concentrated to give methyl 2-(triphenylphosphoranylidene)acetate (7.5 g, 93% yield) as a white solid. A solution of 3-chloro-2-methylbenzaldehyde (0.7 g, 4.53 mmol) and 2-(triphenylphosphoranylidene)acetate (1.817 g, 5.43 mmol) in MeOH (22.6 ml) was stirred at room temperature for 2 h. The mixture was concentrated and purified by flash chromatography (0-30% ethyl acetate:hexanes) to afford the title compound (0.23 g, 24% yield) as a clear colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J=15.9 Hz, 1H), 7.47-7.40 (m, 2H), 7.17-7.15 (m, 1H), 6.33 (d, J=15.9 Hz, 1H), 3.83 (s, 3H), 2.48 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (0-30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-1a3eff1ca73d4c74974c336d69c1f395
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…