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

HRID 2378523Notes

Reaction equation

HRID 2378523 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) and mixing the mixture 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, 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. additionmixing the mixture under ice cooling
  3. stirringfurther stirred for 1.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionextracted with diethyl ether (200 ml)
  6. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
  7. customThe organic layer was dried
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4c86143a820244ef9a57feb168f7cc71
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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