Dimethyl Sulfoxide → Benzenepropanal

HRID 635248Notes

Reaction equation

HRID 635248 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][CH2:19][OH:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]1([CH2:17][CH2:18][CH:19]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 31234BenzenepropanolHCID 65578Oxalyl chloride

Product 1

HCID 7707BenzenepropanalYield 47.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (2.90 g; 2.29 mmol) in methylene chloride (50 mL), cooled to −78° C., was treated with dimethylsulfoxide (3.4 mL) in 10 mL of methylene chloride. After stirring for 5 minutes, 3-phenyl-1-propanol (2.72 g; 20 mmol) in 20 mL of methylene chloride was added, and the resulting mixture was stirred at −78° C. for 15 minutes, treated with 14 mL of triethylamine, stirred an additional 15 minutes, and poured into 100 mL of water. The layers were separated, the organic phase was dried and concentrated, and the crude residue was purified on a silica gel column, eluting with 10% ethyl acetate in hexane, to obtain 1.27 g (47%) of the aldehyde as a clear oil. 1H NMR (300 MHz, CDCl3): δ2.80 (m, 2H); 2.98 (m, 2H); 7.27 (m, 5H); 9.81 (s, 1H).

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 15 minutes
  2. stirringstirred an additional 15 minutes
  3. customThe layers were separated
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customthe crude residue was purified on a silica gel column
  7. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6eefa8402d09459b9d449a07086dade7
Source dataset
uspto-grants-2001_02
Patent number
US06187796B1

Reaction notes

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