Water → 3-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

HRID 1640726Notes

Reaction equation

HRID 1640726 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:10])[CH2:5][CH:6]([OH:9])CO.O>ClCCl>[OH:10][C:4]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH2:3][O:2][CH3:1])[CH2:5][CH:6]=[O:9]

Participants

4

Reactant 2

HCID 962Water2×HCID 596356585-Methoxy-4-phenyl-pentane-1,2,4-triol

Product 1

HCID 596356773-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

NalO4 (5.20 g) was added to a mixture of 5-methoxy-4-phenyl-pentane-1,2,4-triol (1.10 g), dichloromethane (10 mL), and water (5 mL) chilled in an ice bath. The mixture was stirred vigorously while warming to ambient temperature in the cooling bath and further stirred at this temperature overnight. Then, water (20 mL) and dichloromethane (50 mL) were added, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic phases were washed with water and dried (MgSO4). After removal of the solvent, the title compound was yielded which was directly submitted to the next reaction step (glycol cleavage).

Workup

  1. temperaturechilled in an ice bath
  2. stirringfurther stirred at this temperature overnight
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-40176ecfaf5a4f0c8e09dee6dea8c2ec
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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