Dimethylformamide → 2-phenethylbenzaldehyde

HRID 1106798Notes

Reaction equation

HRID 1106798 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 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 78603o-Phenethylbenzoic acid

Product 1

HCID 107271692-phenethylbenzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A mixture of 2-phenethylbenzoic acid (11.3 g), oxalyl chloride (5.2 ml), DMF (0.2 ml) and dichloromethane (100 ml) was stirred for 1.5 hours. The solvent was evaporated, diglyme (75 ml) added and the mixture cooled to -70° C. Lithium tri-(tert-butoxy)aluminium hydride (100 ml, 0.5M solution in diglyme) was added dropwise over 45 minutes maintaining the reaction temperature below -60° C. The reaction was stirred at -70° C. for 1 hour and poured into a 2N HCl and ice mixture. The mixture was extracted with iso-hexane (3×100 ml). The extracts were washed with saturated aqueous sodium hydrogen carbonate, water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by MPLC eluting with dichloromethane/ iso-hexane (1: 1) to give 2-(phenethyl)benzaldehyde (7.77 g).

Workup

  1. customThe solvent was evaporated
  2. additiondiglyme (75 ml) added
  3. additionLithium tri-(tert-butoxy)aluminium hydride (100 ml, 0.5M solution in diglyme) was added dropwise over 45 minutes
  4. temperaturemaintaining the reaction temperature below -60° C
  5. stirringThe reaction was stirred at -70° C. for 1 hour
  6. additionpoured into a 2N HCl and ice mixture
  7. extractionThe mixture was extracted with iso-hexane (3×100 ml)
  8. washThe extracts were washed with saturated aqueous sodium hydrogen carbonate, water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by MPLC
  13. washeluting with dichloromethane/ iso-hexane (1: 1)

Sources & evidence

ORD record
ord-a6c01955ca9c40ffa6cbd663e9c6dd47
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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