p-Toluenesulfonic acid → 1-(4-Hydroxyphenyl)ethyl butyrate

HRID 344798Notes

Reaction equation

HRID 344798 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[C:12]([O:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C2CCCCO2)=[CH:22][CH:21]=1)[CH3:19])(=[O:16])[CH2:13][CH2:14][CH3:15]>CO>[C:12]([O:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[CH3:19])(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 541704431-(4-(Tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate

Product 1

HCID 541339111-(4-Hydroxyphenyl)ethyl butyrateYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol was dissolved 0.1 mole of the R-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate, to which 1.1 g of pyridinum, p-toluenesulfonate, and the mixture was subjected to reaction at room temperature for 2 hours. Then, methanol was distilled under reduced pressure, 200 ml of ether was added thereto, and it was washed with water. The resulting ether layer was dried with anhydrous magnesium sulfate, and ether was distilled under reduced pressure to give R-form of 1-(4-hydroxyphenyl)ethyl butyrate (yield: 11%).

Workup

  1. distillationThen, methanol was distilled under reduced pressure, 200 ml of ether
  2. additionwas added
  3. washit was washed with water
  4. dry with materialThe resulting ether layer was dried with anhydrous magnesium sulfate, and ether
  5. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-4188eb2a36f249f3be70df3177bd47da
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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