Dichloromethane → Phenylpropiolic Acid

HRID 1906139Notes

Reaction equation

HRID 1906139 reaction equation
[C:1]1([C:7]#[C:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12](Cl)Cl.S(Cl)(Cl)=O>CO>[C:1]1([C:7]#[C:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]#[C:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 69475Phenylpropiolic Acid

Product 2

HCID 69475Phenylpropiolic AcidHCID 138378Phenylpropynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylpropiolic acid was synthesized according to the method as described in J. Chem. Soc., Vol. 83, page 1154. To a mixture of 42 g of phenylpropiolic acid and 50 ml of methylene chloride was added 42 ml of thionyl chloride, and the mixture was mildly refluxed by heating on a water bath. After the completion of the generation of gas, the solvent and excessive thionyl chloride were distilled off under reduced pressure. The pale yellow liquid thus obtained was gradually added to 300 ml of methanol under cooling with ice. After being allowing to stand overnight, the solvent was distilled off under a reduced pressure, and the residual liquid was washed with water and dried to obtain 44.5 g of almost pure methyl phenylpropiolate.

Workup

  1. temperaturethe mixture was mildly refluxed
  2. temperatureby heating on a water bath
  3. distillationAfter the completion of the generation of gas, the solvent and excessive thionyl chloride were distilled off under reduced pressure
  4. customThe pale yellow liquid thus obtained
  5. temperatureunder cooling with ice
  6. distillationthe solvent was distilled off under a reduced pressure
  7. washthe residual liquid was washed with water
  8. customdried

Sources & evidence

ORD record
ord-2702795a56244b5ca0368bea2b2241ce
Source dataset
uspto-grants-1987_03
Patent number
US04650749

Reaction notes

Loading…