Acetone → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 1645552Notes

Reaction equation

HRID 1645552 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[CH3:8][C:9]([CH3:11])=O.Cl(O)(=O)(=O)=O.N>>[CH3:8][C:9]1([CH3:11])[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 222AmmoniaHCID 24247Perchloric AcidHCID 78432Trimethylolmethane

Product 1

HCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolYield 85.8%

Procedure

A mixture of 2-(hydroxymethyl)-1,3-propanediol (4.09 g, 38.5 mmol), acetone (130 ml, 1768 mmol) and 70% perchloric acid (1.37 g, 9.55 mmol) was stirred at room temperature for 21 hours. After the pH of the reaction mixture was adjusted with concentrated aqueous ammonia to 9, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate=1/3) to obtain the title compound (4.83 g, yield: 85.8%) as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-3e97b91fbe1a4a5fb75566c0902f1ed0
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

Loading…