2-Mercaptoethanol → HCID 19817904, compound

HRID 971822Notes

Reaction equation

HRID 971822 reaction equation
[O-]CC.[Na+].[SH:5][CH2:6][CH2:7][OH:8].[CH:9]([CH:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:10]>C(O)C>[OH:8][CH2:7][CH2:6][S:5][CH:11]([CH:9]=[CH2:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 2723922Sodium ethoxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 19817904HCID 19817904, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 408 g (6 moles) of sodium ethoxide in 3 l of absolute ethanol, cooled to 0° to 5° C., was added dropwise 476 g (6.1 moles) of 2-mercaptoethanol. Following addition, the solution was stirred for an additional hour at room temperature and then 915 g (6.0 moles) of vinylbenzyl chloride (60 percent m, 40 percent p) was added dropwise. After addition, the mixture was refluxed for 1 hour and was then cooled to room temperature. The sodium chloride was removed by filtration and the solvent was removed on a rotary evaporator to give the product as a yellow oil. The oil was distilled via a short path column to give 626.5 g (54 percent) of the desired product (b.p. 110° to 120° C. and 7 microns Hg).

Workup

  1. additionaddition
  2. additionAfter addition
  3. temperaturethe mixture was refluxed for 1 hour
  4. temperaturewas then cooled to room temperature
  5. customThe sodium chloride was removed by filtration
  6. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-7133d732bef74deeadd6911db22b5aed
Source dataset
uspto-grants-1979_07
Patent number
US04161407

Reaction notes

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