Dimethyl Sulfoxide → 2-Methyl-4-octanone

HRID 1646537Notes

Reaction equation

HRID 1646537 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH:12]([CH2:14][CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][CH:12]([CH2:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1424702-Methyloctan-4-ol

Product 1

HCID 5225662-Methyl-4-octanoneYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of oxalyl chloride (4.2 ml, 49 mmol) in dry DCM (200 ml) was cooled to -78° C. under argon. Dimethylsulphoxide (6.9 ml, 98 mmol) was added slowly and the mixture stirred for 5 min. 2-Methyloctan-4-ol (6.4 g, 44 mmol) was added and the mixture stirred for 20 min. Triethylamine (30.7 ml, 0.22 ml) was added and after 5 min. the mixture was allowed to warm up to room temperature. Water (100 ml) was added, the organic layer separated and the aqueous layer extracted with DCM. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and concentrated to give 2-methyloctan-4-one (5.0 g, 79%) as a waxy oil.

Workup

  1. stirringthe mixture stirred for 20 min
  2. customthe organic layer separated
  3. extractionthe aqueous layer extracted with DCM
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c422fa8610444c9aef714a58ab336bc
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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