Methanol → Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

HRID 464727Notes

Reaction equation

HRID 464727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:8][C:7](=[O:9])[CH:6]=[CH:5][C:4]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 145483-(3,4-Dichlorophenyl)prop-2-enoic acid

Product 1

HCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

Procedure

A suspension of 300 g of 3,4-dichlorocinnamic acid (J. Org. Chem., 26:2991 (1961)) and 25 ml of concentrated sulfuric acid in 1.7 liters of methanol is heated to reflux for 24 hours. The solution is concentrated, cooled, and filtered to give as a white solid, 3,4-dichlorocinnamic acid methyl ester, mp 114°-15° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe solution is concentrated
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a808aaa7e6c843c593a7d4eb037e86bf
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

Loading…