Ethanol → 1,1-Dimethoxy-7-mercapto-3,7-dimethyloctane

HRID 1605128Notes

Reaction equation

HRID 1605128 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][CH:5]([CH3:13])[CH2:6][CH2:7][CH2:8][C:9](Cl)([CH3:11])[CH3:10].NC(N)=[S:18].C(O)C.[OH-].[Na+]>CCOCC.O>[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][CH:5]([CH3:13])[CH2:6][CH2:7][CH2:8][C:9]([SH:18])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 215493461,1-Dimethoxy-7-chloro-3,7-dimethyloctane

Product 1

HCID 215493991,1-Dimethoxy-7-mercapto-3,7-dimethyloctane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g. of 1,1-dimethoxy-7-chloro-3,7-dimethyloctane, one equivalent of thiourea and 100 ml. of 95% ethanol is refluxed for about 24 hours. Then a solution of 1.5 equivalents of sodium hydroxide in 50 ml. of water is added and the mixture refluxed for about 2 hours. After cooling to about room temperature, the solution is carefully acidified and ether is added. The organic layer is separated, washed with water, dried over calcium sulfate and evaporated to give 1,1-dimethoxy-7-mercapto-3,7-dimethyloctane which is purified by distillation.

Workup

  1. additionA mixture of 10 g
  2. temperaturethe mixture refluxed for about 2 hours
  3. temperatureAfter cooling to about room temperature
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over calcium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-9afca46471334ce1adaab0a246dc634f
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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