Dimethyl Sulfoxide → Benzenepentanal

HRID 1107143Notes

Reaction equation

HRID 1107143 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 615235-Phenyl-1-pentanolHCID 65578Oxalyl chloride

Product 1

HCID 561886BenzenepentanalYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 15.9 mL (182.65 mmol, 1.2 eq) of oxalyl chloride in 300 mL of CH2Cl2 at -78° C. under argon is added dropwise 25.9 mL (365.3 mmol, 2.4 eq) of DMSO in 40 mL of CH2Cl2. After stirring for 1 hour at -78° C., 25 g (152.21 mmol) of 5-phenyl-1-pentanol dissolved in 40 mL of CH2Cl2 is added dropwise. After stirring for 2 hour at -78° C., 106 mL (761.03 mmol, 5 eq) of triethylamine is added dropwise. This then stirred at -78° C. for 1 hours then at 25° C. for overnight. The reaction is partitioned between CH2Cl2 and 1 N HCl. The organic layer is washed well with water, dried over anhydrous MgSO4 and concentrated in vacuo to afford 23.52 g (95%) of 5-phenylpentanal in the form of a yellow oil.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring for 2 hour at -78° C.
  3. stirringThis then stirred at -78° C. for 1 hours
  4. waitat 25° C. for overnight
  5. customThe reaction is partitioned between CH2Cl2 and 1 N HCl
  6. washThe organic layer is washed well with water
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5fcad51338e4ff9a4e611693fe684cd
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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