Ethanol → HCID 59479194, compound

HRID 450745Notes

Reaction equation

HRID 450745 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14])[CH:9]=[CH:10][CH:11]=1.[Cl-].[Ca+2].[Cl-].C(O)C.[BH4-].[Na+]>O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 10892196HCID 10892196, compound

Product 1

HCID 59479194HCID 59479194, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.01 g of diethyl [3-(1,3-dioxolan-2-yl)phenyl]malonate, 2.89 g of calcium chloride, and 50 ml of ethanol was added 2.47 g of sodium borohydride under ice-cooling, followed by stirring at the same temperature for 2 hours and at room temperature for 4 hours. To the reaction solution was added 10 ml of water at room temperature, followed by stifling for 30 minutes. The insoluble material was separated by filtration using Celite, and the filtrate was concentrated under reduced pressure to obtain 0.76 g of 2-[3-(1,3-dioxolan-2-yl)phenyl]propane-1,3-diol as a colorless oily substance.

Workup

  1. temperaturecooling
  2. waitby stifling for 30 minutes
  3. customThe insoluble material was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-299a6c90b72246cda68011f0452f7c1c
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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