Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 1-(4-Hydroxyphenyl)ethyl butyrate

HRID 344797Notes

Reaction equation

HRID 344797 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:23][CH:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C2CCCCO2)=[CH:28][CH:27]=1)[CH3:25])(=[O:22])[CH2:19][CH2:20][CH3:21]>CO>[C:18]([O:23][CH:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[CH3:25])(=[O:22])[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 541704431-(4-(Tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate

Product 1

HCID 541339111-(4-Hydroxyphenyl)ethyl butyrateYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol was dissolved 0.1 mole of the S-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate, 1.1 g of pyridinium p-toluenesulfonate was added thereto, and the mixture was subjected to reaction at room temperature for 2 hours. Then, methanol was distilled under reduced pressure, to which 200 ml of ether was added, and the mixture was washed with water. The resulting ether layer was dried with anhydrous magnesium sulfate, and ether was distilled under reduced pressure to give S-form of 1-(4-hydroxyphenyl)ethyl butyrate (yield: 13%).

Workup

  1. additionwas added
  2. customthe mixture was subjected to reaction at room temperature for 2 hours
  3. distillationThen, methanol was distilled under reduced pressure, to which 200 ml of ether
  4. additionwas added
  5. washthe mixture was washed with water
  6. dry with materialThe resulting ether layer was dried with anhydrous magnesium sulfate, and ether
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-f335a3f28ccc4b94847390381846f88d
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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