Hydrogen Sulfide → 2-Methyl-1-sulfanylheptan-2-OL

HRID 1105649Notes

Reaction equation

HRID 1105649 reaction equation
[SH2:1].C(NCC)C.[CH3:7][C:8]1([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][O:9]1>CO>[OH:9][C:8]([CH3:7])([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][SH:1]

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 8021DiethylamineHCID 5590732-Methyl-2-pentyloxirane

Product 1

HCID 135068602-Methyl-1-sulfanylheptan-2-OL

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Hydrogen sulphide is passed into 150 ml. of methanol with ice cooling, until the weight increase amounts to 3.2 g. A solution of 370 mg. of diethylamine in 11 ml. of methanol is added thereto, followed by 4.8 g. of 2-methyl-2-pentyloxirane in 18 ml. of methanol. Hydrogen sulphide gas again is passed into the solution for 15 minutes and the solution is permitted to stand for 12 hours at room temperature. The solvent is distilled off and the residue dissolved in 50 ml. of petroleum ether (b.p.=50°-70° C.), washed with water and dried with sodium sulphate. The solvent is distilled off and 2-hydroxy-2-methyl-heptanethiol is obtained as a colorless residual liquid.

Workup

  1. distillationThe solvent is distilled off
  2. dissolutionthe residue dissolved in 50 ml
  3. washof petroleum ether (b.p.=50°-70° C.), washed with water
  4. dry with materialdried with sodium sulphate
  5. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-412f38d2eaae49939d838fb99560b71d
Source dataset
uspto-grants-1982_01
Patent number
US04309441

Reaction notes

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