Water → 2-[(Butylthio)methylene]-6-ethylcyclohexanone

HRID 1438914Notes

Reaction equation

HRID 1438914 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][C:5](=[CH:9]O)[C:4]1=[O:11])[CH3:2].[CH2:12]([SH:16])[CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:12]([S:16][CH:9]=[C:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:1][CH3:2])[C:4]1=[O:11])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8012ButanethiolHCID 70624727HCID 70624727, compound

Product 1

HCID 537663082-[(Butylthio)methylene]-6-ethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-ethyl-6-(hydroxymethylene)cyclohexanone (43.0 g, 0.277 mole), described in Example 2, butylmercaptan (28.6 g, 0.318 mole) and p-toluenesulfonic acid (50 mg) in dry benzene (200 ml) is heated at reflux under nitrogen for 4 hr using a Dean-Stark water separator. The reaction mixture is cooled and washed with saturated aqueous sodium bicarbonate (50 ml), water and brine, then dried (MgSO4). After removal of the solvent at reduced pressure the residue is distilled to give the title compound, bp 110° - 115° C/1.5 mm, nmr (CDCl3) δ 0.92 (6H), 7.5 (m,1H).

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 4 hr
  3. temperatureThe reaction mixture is cooled
  4. washwashed with saturated aqueous sodium bicarbonate (50 ml), water and brine
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent at reduced pressure the residue
  7. distillationis distilled

Sources & evidence

ORD record
ord-4b10890d253445b8ac7b2d134399e91f
Source dataset
uspto-grants-1977_11
Patent number
US04057559

Reaction notes

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