Dimethyl Sulfoxide → Methyl 4-formylcyclohexane-1-carboxylate

HRID 129276

Reaction equation

HRID 129276 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl.O>[CH:12]([CH:13]1[CH2:14][CH2:15][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]1)=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Product 1

HCID 11252253Methyl 4-formylcyclohexane-1-carboxylateYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

Dimethyl sulphoxide (0.65 ml) in dry dichloromethane (5 ml) was added to a solution of oxalyl chloride (0.363 ml) in dichloromethane (5 ml) at -70° C. under a stream of nitrogen. After 5 minutes stirring a solution of methyl 4-hydroxymethylcyclohexanecarboxylate (0.64 g) in dichloromethane (5 ml) was added dropwise. The reaction mixture was stirred for 30 minutes at -70° C. Triethylamine (2.60 ml) was then added and the reaction mixture allowed to warm to room temperature during a period of 3 hours. After pouring into water (100 ml) the organic phase was washed with dilute hydrochloric acid, sodium bicarbonate solution and brine before drying over magnesium sulphate. Evaporation in vacuo gave methyl 4-formylcyclohexanecarboxylate (0.58 g) as a mixture of cis- and trans-isomers.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to room temperature during a period of 3 hours
  3. washwas washed with dilute hydrochloric acid, sodium bicarbonate solution and brine
  4. dry with materialbefore drying over magnesium sulphate
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-6d2e82a815f641d0a89bac57b62e8a81
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Linked notes

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