Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl Ester

HRID 1271255Notes

Reaction equation

HRID 1271255 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13]C1CCCCO1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 69357347HCID 69357347, compound

Product 1

HCID 865924602-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl EsterYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.00 g of 2-[4-(2-tetrahydropyranyloxy)-(Z)-2-buten-1-yloxy]acetic acid tert-butyl ester in 30 ml of methanol, 88 mg of pyridinium p-toluenesulfonate was added and the mixture was heated at reflux for 3 hours. The solvent was evaporated under reduced pressure and the reaction solution was extracted with ethyl acetate after adding water. After the extract was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 420 mg of the desired compound as an oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. additionafter adding water
  6. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b987705a7c1448129d43223517a3fb95
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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