Hydrochloric Acid → 3-(Benzyloxy)propanal

HRID 568970Notes

Reaction equation

HRID 568970 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][CH2:19][CH2:20][CH2:21][OH:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>ClCCl.C(N(CC)CC)C>[CH2:11]([O:18][CH2:19][CH2:20][CH:21]=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 3479713-Benzyloxy-1-propanol

Product 1

HCID 108882613-(Benzyloxy)propanal

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-50 °C

Procedure

Under nitrogen, a solution of DMSO (8.4 mL, 118 mmoles) in dry dichloromethane (125 mL) is cooled to -60° C., and oxalyl chloride (5 mL, 59 mmoles) in CH2Cl2 (40 mL) is added slowly. After stirring for 5 min at -50° C., 3-benzyloxy-1-propanol (14), 8.9 g, 53.7 mmoles) in CH2Cl2 (27 mL) is added at -60° C. Stirring is continued for 15 min, then triethylamine (47 mL) is added slowly at -60° C. After 5 min at this temperature, the mixture is allowed to warm up to room temperature. After addition of 0.5N HCl and phase separation, the organic phase is washed with water until neutral. Drying (Na2SO4) and evaporation gives the crude aldehyde as an oil: 10.6 g. Distillation under vacuum gives pure 15: 6.54 g (74%), bp 170° C. (15 mm Hg).

Workup

  1. stirringStirring
  2. waitis continued for 15 min
  3. waitAfter 5 min at this temperature
  4. temperatureto warm up to room temperature
  5. washthe organic phase is washed with water until neutral
  6. customDrying
  7. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-a21bbec554da42dc89907fe23201e65d
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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