Dimethyl Sulfoxide → Benzenepropanal

HRID 2271065Notes

Reaction equation

HRID 2271065 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) δ 2.80 (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-bcaf588444a9401795ba30d9b13582a6
Source dataset
uspto-grants-2001_12
Patent number
US06333340B1

Reaction notes

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