Dimethyl Sulfoxide → HCID 20432036, compound

HRID 2412587Notes

Reaction equation

HRID 2412587 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O-:7])=[O:6].[K+].[CH:13]([CH:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:14].CS(C)=O>O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH:15]([CH:13]=[CH2:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 23682497HCID 23682497, compound

Product 1

HCID 20432036HCID 20432036, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

129.4 g of potassium 3,5-dihydroxybenzoate and 102.7 g of vinylbenzyl chloride were added to 700 ml of dimethylsulfoxide and stirred and reacted at 40° C. for 4 days. Then, 1,500 ml of water was added thereto, and the resulting mixture was extracted with 500 ml of ethyl acetate. After distilling off ethyl acetate, recrystallization of the residue from an ethyl acetate-toluene mixture solvent yielded 152 g of vinylbenzyl 3,5-dihydroxybenzoate (m.p. 117°-119° C.).

Workup

  1. customreacted at 40° C. for 4 days
  2. extractionthe resulting mixture was extracted with 500 ml of ethyl acetate
  3. distillationAfter distilling off
  4. customethyl acetate, recrystallization of the residue from an ethyl acetate-toluene mixture solvent

Sources & evidence

ORD record
ord-a728c3d4a5db4ddfbd0259654cf85598
Source dataset
uspto-grants-1985_01
Patent number
US04493884

Reaction notes

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