Dimethyl Sulfoxide → Vinylbenzyl p-hydroxybenzoate

HRID 2412585Notes

Reaction equation

HRID 2412585 reaction equation
[CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[OH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O-:18])=[O:17])=[CH:14][CH:13]=1.[Na+].CS(C)=O>O>[OH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:18][CH:3]([CH:1]=[CH2:2])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 16219477Sodium 4-hydroxybenzoate

Product 1

HCID 20432038Vinylbenzyl p-hydroxybenzoateYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

71.5 g of vinylbenzyl chloride and 75.0 g of sodium p-hydroxybenzoate were added to 250 ml of dimethylsulfoxide and stirred and reacted at 40° C. for 4 days. Then 1,000 ml of water was added thereto, and the resulting mixture was extracted with 200 ml of ethyl acetate. After distilling off ethyl acetate, recrystallization of the residue from benzene-hexane mixture solvent yielded 110 g of vinylbenzyl p-hydroxybenzoate (m.p. 83°-85° C.).

Workup

  1. customreacted at 40° C. for 4 days
  2. extractionthe resulting mixture was extracted with 200 ml of ethyl acetate
  3. distillationAfter distilling off
  4. customethyl acetate, recrystallization of the residue from benzene-hexane mixture solvent

Sources & evidence

ORD record
ord-739e1f7ac7e646cd82e3c8d4326df2ef
Source dataset
uspto-grants-1985_01
Patent number
US04493884

Reaction notes

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