Water → 7-Methylthio-3,7-dimethyloctan-1-al

HRID 1605142Notes

Reaction equation

HRID 1605142 reaction equation
[CH3:1][S:2][C:3]([CH3:13])([CH3:12])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH2:9][OH:10].C(N(CC)CC)C.O.CCCCCC>CS(C)=O>[CH3:1][S:2][C:3]([CH3:12])([CH3:13])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 8471TriethylamineHCID 215493537-Methylthio-3,7-dimethyloctan-1-ol

Product 1

HCID 215493787-Methylthio-3,7-dimethyloctan-1-al

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 2.04 g. (10 mmol.) of 7-methylthio-3,7-dimethyloctan-1-ol in 25 ml. of freshly distilled dimethylsulfoxide, under nitrogen at 20°, is added via syringe 11.2 ml. (80 mmol.) of triethylamine while stirring vigorously. Sulfur trioxide-2 pyridine complex (10.28 g., 64 mmol.) in dimethylsulfoxide (50 ml.) is added slowly to the mixture via dropping funnel under the same conditions. After addition is complete, the reaction mixture is stirred for 5 minutes and poured into cold water. Hexane is added and the organic layer separated, washed well with water and dried over calcium sulfate. Evaporation of the solvent at reduced pressure affords 7-methylthio-3,7-dimethyloctan-1-al.

Workup

  1. additionAfter addition
  2. customthe organic layer separated
  3. washwashed well with water
  4. dry with materialdried over calcium sulfate
  5. customEvaporation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-79856178340d4dd8a22f1a10de38eaed
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

Loading…