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

HRID 1607401Notes

Reaction equation

HRID 1607401 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1([O:16][CH2:15][CH2:14][O:13]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH2:15]1[CH2:14][O:13][C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([CH2:5][CH2:4][CH2:3][OH:2])[O:16]1

Participants

5

Reactant 3

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

Product 1

HCID 223445572-(3-Hydroxypropyl)-2-phenyl-1,3-dioxolaneYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.7 g of the ester compound obtained in 20 ml of dry diethyl ether was added 0.7 g of lithium aluminum hydride under ice-cooling, the mixture was stirred for 1 hour at 0° C., and then heated under reflux for 17 hours. After cooling, the reaction mixture was treated successively with an aqueous diethyl ether solution and water, and the precipitate was filtered off. The filtrate was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/ethyl acetate=10/1 by volume) to obtain 1.3 g of 4,4-ethylenedioxy-4-phenylbutyl alcohol.

Workup

  1. temperaturecooling
  2. temperatureheated
  3. temperatureunder reflux for 17 hours
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered off
  6. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/ethyl acetate=10/1 by volume)

Sources & evidence

ORD record
ord-5e1621196ae6435499e2def7da590537
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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