Acetone → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

HRID 2308889Notes

Reaction equation

HRID 2308889 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].[CH3:9][C:10]([CH3:12])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(=O)C.[Na+]>O>[OH:1][CH2:2][C:3]1([CH3:4])[CH2:7][O:8][C:10]([CH3:12])([CH3:9])[O:6][CH2:5]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6502TrimethylolethaneHCID 517045Sodium AcetateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxaneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 g of 1,1,1-tris(hydroxymethyl)ethane (Aldrich Chemical Co., Milwaukee, WI), 85 ml of acetone and 80 ml of petroleum ether (b.p. 30°-75° C.) was acidified with 1.0 g of p-toluenesulfonic acid monohydrate and this mixture was refluxed for 24 hours with removal of water by azeotropic distillation. This was followed by neutralization with 1 g of sodium acetate and complete drying with anhydrous sodium sulfate. The liquid was filtered and the solvents removed under reduced pressure. The residue was distilled under vacuum to give 5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane in 90% yield.

Workup

  1. dry with materialcomplete drying with anhydrous sodium sulfate
  2. filtrationThe liquid was filtered
  3. customthe solvents removed under reduced pressure
  4. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-271307e06b444cd48f1ea39f5a902419
Source dataset
uspto-grants-1987_09
Patent number
US04691059

Reaction notes

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