Benzyl Chloride → 1,3-Dioxolane, 4-benzyloxymethyl-2,2-dimethyl-5-hydroxymethyl-

HRID 1982238Notes

Reaction equation

HRID 1982238 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][CH:5]([CH2:7][OH:8])[CH:4]([CH2:9][OH:10])[O:3]1.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:11])[O:3][CH:4]([CH2:9][OH:10])[CH:5]([CH2:7][O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:6]1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 318275[5-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Product 1

HCID 5611801,3-Dioxolane, 4-benzyloxymethyl-2,2-dimethyl-5-hydroxymethyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, benzyl ethers may be used to protect --OH groups. For example, 2,2-dimethyl-4,5-di(hydroxymethyl)-1,3-dioxolane (8 g, 0.2 mol) is heated at reflux with benzyl chloride (25 g, 0.2 mol) and K2CO3 (25 g, 0.2 mol) in 100 ml ethanol. The product is added to aqueous NaOH, extracted with ether, and purified by silica gel chromatography to yield 2,2-dimethyl-4-hydroxymethyl-5-benzyloxymethyl-1,3-dioxolane.

Workup

  1. extractionextracted with ether
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-48e834ec84c142f0afbace7f19231c80
Source dataset
uspto-grants-1986_06
Patent number
US04595690

Reaction notes

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