4-Toluenesulfonyl chloride → Ethyl 2-(4-vinylphenoxy)isobutyrate

HRID 1605119Notes

Reaction equation

HRID 1605119 reaction equation
O[CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)[CH3:3].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=[CH2:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 103599Ethyl 2-[4-(1-hydroxyethyl)phenoxy]-2-methylpropanoate

Product 1

HCID 104107Ethyl 2-(4-vinylphenoxy)isobutyrate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 116 g. of ethyl 2-[4-(1-hydroxyethyl)phenoxy]-2-methylpropionate and 92 g. of p-toluenesulfonyl chloride in 500 ml. of pyridine was heated at reflux for three hours, kept at room temperature for about 16 hours and then heated at reflux again for six hours. The reaction mixture was poured into ice water and extracted with hexane. The hexane solution was washed successively with dilute sulfuric acid, 10% potassium bicarbonate, water and saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was distilled at 104°-111°C. (0.03-0.08 mm.) to give60 g. of ethyl 2-(p-vinylphenoxy)-2-methylpropionate.

Workup

  1. additionA mixture of 116 g
  2. temperatureat reflux for three hours
  3. temperatureheated
  4. temperatureat reflux again for six hours
  5. extractionextracted with hexane
  6. washThe hexane solution was washed successively with dilute sulfuric acid, 10% potassium bicarbonate, water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationThe residue was distilled at 104°-111°C. (0.03-0.08 mm.) to give60

Sources & evidence

ORD record
ord-9d0e138a466847e68b01e9ff93c5274b
Source dataset
uspto-grants-1976_04
Patent number
US03948973

Reaction notes

Loading…