Water → 2-(3-Hydroxypropyl)-2-phenyl-1,3-dioxolane

HRID 2299753Notes

Reaction equation

HRID 2299753 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][C:7]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:11][CH2:10][CH2:9][O:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C.CCCCCC>C(OCC)C>[OH:2][CH2:3][CH2:5][CH2:6][C:7]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:9][CH2:10][O:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 100371022-[2-(Methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolaneHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 223445572-(3-Hydroxypropyl)-2-phenyl-1,3-dioxolaneYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-[2-(methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolane (5.00 g) in diethyl ether (15 ml) was added dropwise to a mixture of lithium aluminium hydride (949 mg) and diethyl ether (30 ml) at 0° C. After stirring for 30 minutes, water was added to the reaction mixture carefully and the precipitates were removed by filtration. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain 2-(3-hydroxypropyl)-2-phenyl-1,3-dioxolane (3.81 g, yield 87%) as a colorless oil from an ethyl acetate-hexane (2:3, v/v)-eluted fraction.

Workup

  1. customthe precipitates were removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab1489befeb54c289a06e1cb1e61b58f
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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