Hydroquinone → 7-Methylthio-3,7-dimethyloctan-1-ol

HRID 1605140Notes

Reaction equation

HRID 1605140 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][OH:11])[CH3:8])[CH3:3].C1(C)C=C[C:15]([S:18](O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.CS.[OH-].[Na+]>C(=O)=O.CCOCC>[CH3:15][S:18][C:2]([CH3:3])([CH3:1])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][OH:11]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 878MethanethiolHCID 6101p-Toluenesulfonic acidHCID 8842CitronellolHCID 14798Sodium Hydroxide

Product 1

HCID 215493537-Methylthio-3,7-dimethyloctan-1-ol

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4 g. of citronellol (3,7-dimethyloct-6-en-1-ol), 0.490 g. of p-toluenesulfonic acid and 0.290 g. of hydroquinone is placed in a stainles steel screw cap bomb having an internal volume of 45 ml. The bomb is cooled in dry ice. Methyl mercaptan (9 g.) is introduced directly into the bomb through the valve head. The bomb is sealed, left overnight at room temperature and then heated to 220° in an oil bath for about 72 hours. After cooling in dry ice, the bomb valve is opened and the reaction mixture is carefully poured into 5% aqueous sodium hydroxide solution. Ether is added and the organic layer is separated, washed with 5% NaOH, 5% HCl and water, dired over calcium sulfate and concentrated with vacuo to yield 7-methylthio-3,7-dimethyloctan-1-ol.

Workup

  1. additionA mixture of 4 g
  2. customscrew cap bomb
  3. customThe bomb is sealed
  4. temperatureheated to 220° in an oil bath for about 72 hours
  5. customthe organic layer is separated
  6. washwashed with 5% NaOH, 5% HCl and water
  7. concentrationconcentrated with vacuo

Sources & evidence

ORD record
ord-fd3dbbd02e2d447392885f38ae5c7a71
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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