Water → 2-Methyl-3-(oxan-2-yloxy)propan-1-ol

HRID 329790

Reaction equation

HRID 329790 reaction equation
C([O:9][CH2:10][CH:11]([CH3:20])[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)(=O)C1C=CC=CC=1.[OH-].[Na+].O>CO>[CH3:20][CH:11]([CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[CH2:10][OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 147960471-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane

Product 1

HCID 122906532-Methyl-3-(oxan-2-yloxy)propan-1-olYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane (460 mg; 1.65 mmol) was dissolved in methanol (10 ml), and 1M sodium hydroxide solution (3 ml) and water (10 ml) were added thereto, and the resultant mixture was stirred at room temperature for 5 hours. The reaction mixture was extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous magnesium sulfte. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxy-1-propanol (254 mg; yield, 88%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulfte
  4. customThe solvent was removed by distillation
  5. customthe residue was purified by silica gel column chromatography
  6. additiona mixture of ethyl acetate and benzene (1:4)

Sources & evidence

ORD record
ord-a1140472211246ecbe800f963780362d
Source dataset
uspto-grants-1990_01
Patent number
US04892961

Linked notes

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