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

HRID 1990689Notes

Reaction equation

HRID 1990689 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].CO[C:11]([CH3:13])=[CH2:12].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 6502TrimethylolethaneHCID 83002-Methoxypropene

Product 1

HCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxaneYield 96.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,1,1-Tris(hydroxymethyl)ethane (120.2 g) and 2-methoxypropene (75.0 g) were suspended in acetone (300 ml). After adding one drop of cone, sulfuric acid at 0° C., the mixture was stirred for 1 hour and then at room temperature for additional 2 hours. After distilling off the acetone, a fraction obtained under reduced pressure (1.7 mmHg) at 70° C. was collected to give (1,4,4-trimethyl-3,5-dioxanyl)methan-1-ol (155.2 g).

Workup

  1. waitat room temperature for additional 2 hours
  2. distillationAfter distilling off the acetone
  3. customa fraction obtained under reduced pressure (1.7 mmHg) at 70° C.
  4. customwas collected

Sources & evidence

ORD record
ord-6e19782865644f9eac3536d4c0ad5e41
Source dataset
uspto-grants-2010_01
Patent number
US07645565B2

Reaction notes

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