p-Toluenesulfonic acid → 2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

HRID 1713371Notes

Reaction equation

HRID 1713371 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][CH2:7][OH:8])[CH2:4][OH:5].[CH3:9][C:10]1C=CC(S(O)(=O)=O)=C[CH:15]=1.C(N(CC)CC)C>CC(C)=O>[CH3:9][C:10]1([CH3:15])[O:5][CH2:4][CH:3]([CH2:6][CH2:7][OH:8])[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 110406842-(Hydroxymethyl)butane-1,4-diol

Product 1

HCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanolYield 989.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 31 (160 g, 1.30 mol) and 2,2′-dimethoxypropane (207 g, 1.90 mol) in dry acetone (800 mL) was added p-TsOH (92 g, 0.053 mol) under N2 and stirred at RT for 12 h. To this was added triethylamine drop-wise to neutral pH and then concentrated under vacuum below 35° C. The crude residue was purified by column chromatography over neutral alumina (12% ethyl acetate in pet ether) to give the title compound (84 g, 39%). TLC: Pet ether/EtOAc, 1:1, Rf=0.2

Workup

  1. concentrationconcentrated under vacuum below 35° C
  2. customThe crude residue was purified by column chromatography over neutral alumina (12% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-533e0bcfeaa64c9dbe0d0a6d7f5a7571
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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