Dimethyl Sulfoxide → 3-(Benzyloxy)-5-methylbenzaldehyde

HRID 1486879Notes

Reaction equation

HRID 1486879 reaction equation
CS(C)=O.[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=[C:17]([CH3:19])[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>O>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH:20]=[O:21])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 53805946(3-(Benzyloxy)-5-methylphenyl)methanol

Product 1

HCID 1178270383-(Benzyloxy)-5-methylbenzaldehydeYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of a sulfur trioxide-pyridine complex (2.113 g) and dimethyl sulfoxide (10 mL) was added dropwise to a mixture of (3-(benzyloxy)-5-methylphenyl)methanol (1.01 g), triethylamine (3.08 mL), and dimethyl sulfoxide (5 mL) at room temperature, and the obtained mixture was stirred overnight at room temperature. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with 1 M hydrochloric acid and brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (0.948 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with 1 M hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-56319b3e48204eaca4c73007e6be224c
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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