Oxalyl chloride → 2-phenethylbenzaldehyde

HRID 355787Notes

Reaction equation

HRID 355787 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O>CN(C=O)C.ClCCl>[CH2:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[CH:11]=[O:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 78603o-Phenethylbenzoic acid

Product 1

HCID 107271692-phenethylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A mixture of 2-(phenethyl)benzoic acid (commercially available) (11.3 g), oxalyl chloride (5.2 ml), and DMF (2 drops) in dichloromethane (100 ml) was stirred for 1.5 hours. The resulting solution was evaporated and the residue dissolved in diglyme (75 ml) and cooled to -70° C. Li(OtBu)3H (100 ml of 0.5M solution in diglyme) was added dropwise over 45 minutes and the mixture stirred at -70° C. for 1 hour. The solution was poured into 2N aqueous hydrochloric acid and the mixture extracted with iso-hexane (3×100 ml). The combined extracts were washed with saturated aqueous sodium hydrogen carbonate, water and brine and dried (MgSO4). The solvent was evaporated and the residue purified by medium pressure chromatography on silica gel eluting with a mixture of dichloromethane and iso-hexane (1:1) to give 2-(phenethyl)benzaldehyde acid as a colourless oil (7.77 g).

Workup

  1. customThe resulting solution was evaporated
  2. dissolutionthe residue dissolved in diglyme (75 ml)
  3. additionLi(OtBu)3H (100 ml of 0.5M solution in diglyme) was added dropwise over 45 minutes
  4. stirringthe mixture stirred at -70° C. for 1 hour
  5. additionThe solution was poured into 2N aqueous hydrochloric acid
  6. extractionthe mixture extracted with iso-hexane (3×100 ml)
  7. washThe combined extracts were washed with saturated aqueous sodium hydrogen carbonate, water and brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe residue purified by medium pressure chromatography on silica gel eluting with a mixture of dichloromethane and iso-hexane (1:1)

Sources & evidence

ORD record
ord-7890511d64514cf8957d593140cd8cfe
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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