Dimethylformamide → 2-phenethylbenzaldehyde

HRID 1006005Notes

Reaction equation

HRID 1006005 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 purfied 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. washeluting with dichloromethane/iso-hexane (1:1)

Sources & evidence

ORD record
ord-d871ce94a3c643b7b9db96e38261166a
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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