Thionyl Chloride → 3-Methoxycinnamoyl Chloride

HRID 1419947Notes

Reaction equation

HRID 1419947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8](O)=[O:9].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([Cl:16])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-

Product 1

HCID 543303913-Methoxycinnamoyl Chloride

Procedure

A solution of 3-methoxycinnamic acid (75.0 g, 0.42 mol) in thionyl chloride (250 mL) was heated at reflux for 1 h. The majority of the the thionyl chloride was then distilled off and the resulting residue was treated with dichloromethane and residual thionyl chloride was removed by codistillation to give 3-methoxycinnamic acid chloride of sufficient purity to be used without further purification. Pyridine (186 mL, 2.3 mol) and N,O-dimethylhydroxylamine hydrochloride (45.17 g, 0.46 mol) were added to a 0° C. solution of 3-methoxycinnamic acid chloride(0.42 mol) in dry dichloromethane (500 mL). The solution was stirred for 18 h at room temperature, diluted with dichloromethane (200 mL), and washed sequentially with 1N HCl, saturated sodium bicarbonate, and brine. It was then dried over MgSO4 and concentrated in vacuo to give the title compound as a dark oil (88.43 g, 95%): 1H NMR (300 MHz, CDCl3) δ 3.25 (s, 3H), 3.68 (s, 3H), 3.84 (s, 3H), 6.82-6.86 (m, 1H), 7.00 (d, J=16.1 Hz, 1H), 7.10 (br s, 1H), 7.15-7.20 (m, 1H), 7.32 (t, J=6.6 Hz, 1H), 7.72 (d, J=16.0 Hz, 1H).

Workup

  1. temperatureat reflux for 1 h
  2. distillationThe majority of the the thionyl chloride was then distilled off
  3. additionthe resulting residue was treated with dichloromethane and residual thionyl chloride
  4. customwas removed by codistillation

Sources & evidence

ORD record
ord-0eb8c2f9429b47c58f69646bde04dba0
Source dataset
uspto-grants-1999_03
Patent number
US05889031

Reaction notes

Loading…