Sulfuric Acid → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

HRID 1422465Notes

Reaction equation

HRID 1422465 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].CO[C:11](OC)([CH3:13])[CH3:12].S(=O)(=O)(O)O>CC(C)=O>[CH3:4][C:3]1([CH2:7][OH:8])[CH2:5][O:6][C:11]([CH3:13])([CH3:12])[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 6502Trimethylolethane

Product 1

HCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxaneYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

In a three-necked flaks, 1,1,1-tris(hydroxymethyl)ethane (200 g) and 2,2-dimethoxypropane (260 g) were suspended in acetone (150 g), one droplet of concentrated sulfuric acid was added thereto at 0° C., and then the mixture was stirred for 2 hours. The temperature was changed back to a room temperature, and the mixture was stirred for 2 hours. After acetone was distilled off, a fraction obtained at 70° C. under reduced pressure (1.7 mmHg) was collected to obtain (1,4,4-trimethyl-3,5-dioxanyl)methane-1-ol (192 g).

Workup

  1. customwas changed back to a room temperature
  2. stirringthe mixture was stirred for 2 hours
  3. distillationAfter acetone was distilled off
  4. customa fraction obtained at 70° C. under reduced pressure (1.7 mmHg)
  5. customwas collected

Sources & evidence

ORD record
ord-878cfb7faf93462c9aeddc0a5c8513d8
Source dataset
uspto-grants-2015_01
Patent number
US08927195B2

Reaction notes

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