2-Chloroethanol → Dithiaoctanediol

HRID 1583271

Reaction equation

HRID 1583271 reaction equation
[CH2:1]([SH:4])[CH2:2][SH:3].[CH3:5][OH:6].[CH3:7][O-].[Na+].[CH2:10](Cl)[CH2:11][OH:12]>>[CH2:11]([OH:12])[CH2:10][S:3][CH2:2][CH2:1][S:4][CH2:7][CH2:5][OH:6]

Participants

5

Reactant 4

HCID 342-ChloroethanolHCID 887MethanolHCID 109021,2-EthanedithiolHCID 10942334Sodium Methoxide

Product 1

HCID 78904Dithiaoctanediol

Procedure

In an ice bath, 25 g of dithioglycol was stirred and thereto, was added dropwise 1.1 equivalent of a methanol solution of sodium methoxide. Further, 44 g of ethylene chlorohydrin was added dropwise thereto. After the conclusion of the dropwise addition, the reaction mixture was allowed to stand for 10 hours at a room temperature. Then, sodium chloride deposited was removed by filtration, and the resulting filtrate was concentrated. The thus obtained white crystals were recrystallized from acetone. Melting Point 65° C., Yield 25 g.

Workup

  1. additionAfter the conclusion of the dropwise addition
  2. customThen, sodium chloride deposited was removed by filtration
  3. concentrationthe resulting filtrate was concentrated
  4. customThe thus obtained white crystals were recrystallized from acetone

Sources & evidence

ORD record
ord-2f4cb4a66e9242ea8816a9d8bece51dd
Source dataset
uspto-grants-1985_11
Patent number
US04551419

Linked notes

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