2-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxane → (5,5-Dimethyl-1,3-dioxan-2-yl)methanol

HRID 31566Notes

Reaction equation

HRID 31566 reaction equation
C([O:8][CH2:9][CH:10]1[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][O:11]1)C1C=CC=CC=1.[H][H]>[OH-].[Pd+2].[OH-].C(OCC)(=O)C>[CH3:16][C:13]1([CH3:17])[CH2:14][O:15][CH:10]([CH2:9][OH:8])[O:11][CH2:12]1

Participants

5

Reactant 2

HCID 597925572-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxaneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59792511(5,5-Dimethyl-1,3-dioxan-2-yl)methanolYield 85%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 2-((benzyloxy)methyl)-5,5-dimethyl-1,3-dioxane (7.6 g, 32.2 mmol) obtained by the step (1a) was mixed with 20% palladium hydroxide (700 mg) and ethyl acetate (70 ml). The mixture was stirred in a hydrogen atmosphere overnight. The reaction mixture was allowed to stand for further 5 days in the same hydrogen atmosphere. The reaction vessel was purged with nitrogen, the catalyst was filtered off, and the solvent was distilled off to obtain the title compound (4 g, yield: 85%) as a white solid.

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-fde66b4912064de290f78a6002b54f70
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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