Methanol → HCID 14692797, compound

HRID 1087239Notes

Reaction equation

HRID 1087239 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[OH-].[Na+].CO.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[CH2:15]>COC1C=CC(O)=CC=1.O>[CH:14]([C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=1)[CH2:10][S:1][CH2:2][CH2:3][OH:4])=[CH2:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 170249ar-Vinylbenzyl chloride

Product 1

HCID 14692797HCID 14692797, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 962WaterSolvent

Procedure

A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 78 g (1.0 mole) of 2-mercaptoethanol, 133 g (1.0 mole) of a 30 % aqueous solution of sodium hydroxide and 0.15 liter of methanol. While the mixture was cooled to below 10° C., 152 g (1.0 mole) of m-(chloromethyl)styrene was added dropwise over 3 hours. Then, the reaction mixture was continuously stirred for an additional 3 hours to complete the reaction. Water (1 liter) was added to the reaction mixture to separate it into an oil layer and an aqueous layer. The oil layer was washed with water and distilled under reduced pressure (140°-150 ° C./1-2 mmHg) to give 105 g of 2-(3-vinylbenzylthio)ethanol as a colorless transparent liquid.

Workup

  1. temperatureWhile the mixture was cooled to below 10° C.
  2. customthe reaction
  3. customto separate it into an oil layer
  4. washThe oil layer was washed with water
  5. distillationdistilled under reduced pressure (140°-150 ° C./1-2 mmHg)

Sources & evidence

ORD record
ord-40af544f80cd4d1b91b8f6a6b9a4782a
Source dataset
uspto-grants-1991_07
Patent number
US05034492

Reaction notes

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