Hydrochloric Acid → HCID 20360760, compound

HRID 2082828Notes

Reaction equation

HRID 2082828 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:6].C=O.Cl.[CH:19](Cl)(Cl)[Cl:20]>[Cl-].[Zn+2].[Cl-]>[Cl:20][CH2:19][C:15]1[CH:14]=[CH:13][C:4]([C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:6])=[CH:3][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6212ChloroformHCID 20360800HCID 20360800, compound

Product 1

HCID 20360760HCID 20360760, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of methyl 3-(3-hydroxybenzoyl)propionate in chloroform at -5° to 0° was added paraformaldehyde and zinc chloride. Dry hydrogen chloride was passed through the well-stirred solution until the saturation point was reached and the stirring was continued for a further hour at room temperature. The reaction mixture was then poured into ice-water, the product extracted into dichloromethane and the organic layer washed with water and dried over magnesium sulphate. Evaporation of the dichloromethane gave an oily residue from which methyl 3-(4-chloromethyl-3-hydroxybenzoyl)-propionate was obtained by crystallisation from ethanol.

Workup

  1. waitthe stirring was continued for a further hour at room temperature
  2. extractionthe product extracted into dichloromethane
  3. washthe organic layer washed with water
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the dichloromethane

Sources & evidence

ORD record
ord-16a4978eca6f49708896272d442dc000
Source dataset
uspto-grants-1978_04
Patent number
US04082843

Reaction notes

Loading…