2-Mercaptoethanol → Ethanol, 2-[[(4-ethenylphenyl)methyl]thio]-

HRID 1087238Notes

Reaction equation

HRID 1087238 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.[OH-].[Na+].[SH:13][CH2:14][CH2:15][OH:16]>COC1C=CC(O)=CC=1.O1CCCC1>[CH:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][S:13][CH2:14][CH2:15][OH:16])=[CH:4][CH:5]=1)=[CH2:8]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 14692798Ethanol, 2-[[(4-ethenylphenyl)methyl]thio]-Yield 47.9%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 152 g (1.0 mole) of p-(chloromethyl)styrene, 60 g (1.5 moles) of sodium hydroxide and 0.5 liter of tetrahydrofuran. The resulting mixture was boiled, and 78 g (1.0 mole) of 2-mercaptoethanol was added dropwise over 0.5 hour. The boiling was continued for 3 hours. After cooling to room temperature, the reaction mixture was filtered by the same operation as in Example 1, and distilled under reduced pressure (140-145 ° C./1-2 mmHg) to give 93 g of 2-(4-vinylbenzylthio)ethanol as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered by the same operation as in Example 1
  2. distillationdistilled under reduced pressure (140-145 ° C./1-2 mmHg)

Sources & evidence

ORD record
ord-bec347d5a4bb4994b6538c4da0066876
Source dataset
uspto-grants-1991_07
Patent number
US05034492

Reaction notes

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