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

HRID 652534Notes

Reaction equation

HRID 652534 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-c8ed17b8843442f6846bf09952f14ef4
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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