2,2-Dimethoxypropane → 2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

HRID 1368671Notes

Reaction equation

HRID 1368671 reaction equation
[OH:1][CH2:2][CH:3]([CH2:7][OH:8])[CH2:4][CH2:5][OH:6].CO[C:11](OC)([CH3:13])[CH3:12].C(N(CC)CC)C>O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:6][CH2:5][CH2:4][CH:3]1[CH2:7][O:8][C:11]([CH3:13])([CH3:12])[O:1][CH2:2]1

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 110406842-(Hydroxymethyl)butane-1,4-diol

Product 1

HCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanolYield 41%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,4-dihydroxy-2-hydroxymethylbutane (12 g, 100 mmol) in tetrahydrofuran (25 ml), 2,2-dimethoxypropane (13.5 g, 110 mmol) and p-toluenesulphonic acid monohydrate (0.57 g, 3 mmol) were added. The solution was stirred for 0.5 hour at room temperature and was then neutralised by addition of triethylamine. The solvent was removed and the residue purified by column chromatography on silica gel eluting with chloroform-methanol mixtures to afford 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan as a clear colourless liquid (6.5 g, 41%).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with chloroform-methanol mixtures

Sources & evidence

ORD record
ord-3e52e46a2241468bad5efe9145835a54
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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