Oxalyl chloride → HCID 7021752, compound

HRID 1455982Notes

Reaction equation

HRID 1455982 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl.CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[CH:17]=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 14519881HCID 14519881, compound

Product 1

HCID 7021752HCID 7021752, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (3.6 ml) was added to a solution of 2-benzyloxy-4-methylbenzoic acid (9.02 g) in dichloromethane (20 ml), one drop of DMF was added and the mixture was stirred for 2 hours then evaporated to dryness. The residue was dissolved in diglyme (70 ml) and cooled to -78° C. under argon. Lithium-tri-t-butoxyaluminohydride (78 ml of 0.5M solution in diglyme) was added at such a rate that the temperature did not exceed -60° C. The mixture was stirred below this temperature for 2 hours and was then poured carefully onto ice and acidified with concentrated HCl. The mixture was extracted with diethylether (3×150 ml) and the gum obtained on work up was subjected to chromatography on silica eluted with dichloromethane to give 2-benzyloxy-4-methylbenzaldehyde (3.73 g).

Workup

  1. additionwas added
  2. customthen evaporated to dryness
  3. dissolutionThe residue was dissolved in diglyme (70 ml)
  4. additionLithium-tri-t-butoxyaluminohydride (78 ml of 0.5M solution in diglyme) was added at such a rate that the temperature
  5. customdid not exceed -60° C
  6. stirringThe mixture was stirred below this temperature for 2 hours
  7. additionwas then poured carefully onto ice
  8. extractionThe mixture was extracted with diethylether (3×150 ml)
  9. customthe gum obtained on work
  10. washeluted with dichloromethane

Sources & evidence

ORD record
ord-806167c83eb941b6ab8045e46552dbbe
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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