Water → (Phenylmethoxy)acetaldehyde

HRID 553265Notes

Reaction equation

HRID 553265 reaction equation
O.I([O-])(=O)(=O)=O.[Na+].[CH2:8]([O:15][CH2:16][CH:17]([OH:20])CO)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OCC)(=O)C>[CH2:8]([O:15][CH2:16][CH:17]=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 980723-(Benzyloxy)-1,2-propanediolHCID 23667635Sodium periodate

Product 1

HCID 108989(Phenylmethoxy)acetaldehydeYield 86.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a suspension of water (1055 g) and sodium periodate (406 g) was dropped 3-benzyloxy-1,2-propanediol (366 g, 2.0 mol) at 20 to 25° C. over a period of 21 hours, and the mixture was stirred for 2 hours. Ethyl acetate (495 ml) was added, and the mixture was filtrated and washed. The aqueous layer was extracted with ethyl acetate (825 ml) again, and the organic layers were combined, and washed with a 10% sodium thiosulfate aqueous solution (363 g). The organic layer was treated with phosphoric acid to regulate pH to around 7, then, washed twice with 5% saline (660 g) and dehydrated over anhydrous magnesium sulfate (100 g). Magnesium sulfate was filtrated off, and hydroquinone (1.3 g) was added, the solvent was distilled off, to obtain a title compound (259 g, yield 85.9%).

Workup

  1. filtrationthe mixture was filtrated
  2. washwashed
  3. extractionThe aqueous layer was extracted with ethyl acetate (825 ml) again
  4. washwashed with a 10% sodium thiosulfate aqueous solution (363 g)
  5. additionThe organic layer was treated with phosphoric acid
  6. washwashed twice with 5% saline (660 g)
  7. filtrationMagnesium sulfate was filtrated off
  8. additionhydroquinone (1.3 g) was added
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-f060153d12c446e4b75d911fc89c67a0
Source dataset
uspto-grants-2011_05
Patent number
US07951977B2

Reaction notes

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