Dimethyl Sulfoxide → HCID 18993910, compound

HRID 2412586Notes

Reaction equation

HRID 2412586 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[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:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH:15]([CH:13]=[CH2:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 23671662HCID 23671662, compound

Product 1

HCID 18993910HCID 18993910, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

154.0 g of potassium 2,4-dihydroxybenzoate and 122.3 g of vinylbenzyl chloride were added to 500 ml of dimethylsulfoxide, and stirred at 40° C. for 3 days to react. Then, 1,000 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 a benzene-hexane mixture solvent yielded 140 g of vinylbenzyl 2,4-dihydroxybenzoate (m.p. 52°-54° C.).

Workup

  1. customto react
  2. extractionthe resulting mixture was extracted with 500 ml of ethyl acetate
  3. distillationAfter distilling off
  4. customethyl acetate, recrystallization of the residue from a benzene-hexane mixture solvent

Sources & evidence

ORD record
ord-fd48c4df3c9d466f89f17fa1d1f97cd7
Source dataset
uspto-grants-1985_01
Patent number
US04493884

Reaction notes

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