Acetone → 1,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

HRID 1870088Notes

Reaction equation

HRID 1870088 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[CH3:10][C:11]([CH3:13])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCCCCC>[OH:2][CH2:1][C:3]1([CH2:4][CH3:5])[CH2:8][O:9][C:11]([CH3:13])([CH3:10])[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6510TrimethylolpropaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a 3-liter reaction vessel, 292.1 g (2.18 mol) of trimethylolpropane, 474.0 g (8.17 mol) of acetone, 6.0 g (0.0315 mol) of p-toluene sulfonic acid monohydrate, and 900 ml of hexane were placed and refluxed for 24 hours with removing the formed water off the reaction system. The reaction product was neutralized with aqueous solution of sodium hydroxide, and distilled under a reduced pressure to give 5-hydroxymethyl-5-ethyl-2,2-dimethyl-1,3-dioxane.

Workup

  1. temperaturerefluxed for 24 hours
  2. customwith removing the formed water off the reaction system
  3. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-03f943601b7841a4a586e19547651302
Source dataset
uspto-grants-2000_08
Patent number
US06096692

Reaction notes

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