2-(Benzyloxy) ethanol → (Phenylmethoxy)acetaldehyde

HRID 1168611Notes

Reaction equation

HRID 1168611 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])(O)=O.[K+].[K+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.ClCCl>[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 121412-(Benzyloxy) ethanolHCID 24450Potassium Phosphate, DibasicHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite

Product 1

HCID 108989(Phenylmethoxy)acetaldehydeYield 30.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 300-ml three-necked flask was charged with 15.2 g (0.1 mole) of 2-benzyloxyethanol, 100 ml of dichloromethane and 20 ml of water, and further with 2.6 g (15 mmoles ) of dipotassium hydrogenphosphate and 32 mg (0.15 mmole) of 4-acetoxy-2,2,6,6-tetramethyl-piperidinyl-1-oxy, and the mixture was cooled with ice water to 0 to 5° C. with stirring. To the mixed solution, with stirring, 46.6 g (75 mmoles ) of a 12% aqueous solution of sodium hypochlorite was added dropwise over 2 hours, while care was being taken not to permit the temperature to exceed 20° C. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. To the obtained mixture, 30 ml of a 5% aqueous solution of sodium thiosulfate was added, and the resulting mixture wasstirred for 5 minutes. The organic layer was then separated from the mixture. The organic layer separated was washed with 30 ml of saturated aqueous solution of sodium chloride and the solvent was distilled off. The residue obtained was further subjected to vacuum distillation, to yield 7.5 g of benzyloxyacetaldehyde as a fraction at a boiling point of 118 to 120° C./13 mmHg and 4.6 g of unreacted 2-benzyloxyacetaldehyde as a fraction at a boiling point of 128 to 130° C./13 mmHg (yield of benzyloxyacetaldehyde based on the 2-benzyloxyethanol that had reacted: 71.4%, ratio of recovery of 2-benzyloxyethanol: 30.2%).

Workup

  1. stirringTo the mixed solution, with stirring
  2. customto exceed 20° C
  3. additionAfter completion of the addition
  4. stirringthe mixture was stirred at the same temperature for 30 minutes
  5. customThe organic layer was then separated from the mixture
  6. customThe organic layer separated
  7. washwas washed with 30 ml of saturated aqueous solution of sodium chloride
  8. distillationthe solvent was distilled off
  9. customThe residue obtained
  10. distillationwas further subjected to vacuum distillation

Sources & evidence

ORD record
ord-8f89dec1bb3e4993a4a60fb212530932
Source dataset
uspto-grants-2003_09
Patent number
US06624331B1

Reaction notes

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