Methanol → Benzenepropanoic acid, 4-hydroxy-, methyl ester

HRID 984699Notes

Reaction equation

HRID 984699 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 24386Thionyl Chloride

Product 1

HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Procedure

A solution obtained beforehand by adding thionyl chloride (18.3 ml, WAKO) dropwise to methanol (250 ml) under ice cooling was added dropwise with a solution of 3-(4-hydroxyphenyl)propionic acid (16.6 g, TCI) in methanol (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature and further stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure and then extracted with diethyl ether (200 ml). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 1, 17.95 g).

Workup

  1. customA solution obtained
  2. stirringfurther stirred for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with diethyl ether (200 ml)
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
  6. customThe organic layer was dried
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-22f1f93dd9da48428e31ed6c13548f29
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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