Dimethyl Sulfoxide → 3-Methyl-5-(trifluoromethyl)benzaldehyde

HRID 1194745Notes

Reaction equation

HRID 1194745 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2775612(3-Methyl-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 230362293-Methyl-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution fo oxalyl chloride (2.8 ml) in 20 ml of CH2Cl2 is treated with a solution of dimethyl sulfoxide (DMSO)(5.0 ml) in 15 ml of CH2Cl2 at -60° C. as in Example 11 To this mixture is added the 3-trifluoromethyl-5-methylbenzyl alcohol (5.4 g) in CH2Cl2 (20 ml) followed by 20 ml of triethlyamine. Appropriate reaction conditions and work-up as in Example 11 afforded 3-trifluoro- methyl-5-methylbenzaldehyde.

Workup

  1. customAppropriate reaction conditions

Sources & evidence

ORD record
ord-c20a28d229b84864ba030f1b779000e1
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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