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

HRID 931692

Reaction equation

HRID 931692 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].CO[CH:12](OC)[CH3:13].[CH2:16](N(CC)CC)C>O1CCCC1.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:4]([C:3]1([CH2:8][OH:9])[CH2:6][O:7][C:12]([CH3:13])([CH3:16])[O:2][CH2:1]1)[CH3:5]

Participants

7

Reactant 3

HCID 6510TrimethylolpropaneHCID 8471TriethylamineHCID 107951,1-Dimethoxyethane

Product 1

HCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-Yield 95%

Reagents, catalysts & solvents 3

HCID 61578Diammonium molybdateCatalystHCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Trimethylolpropane (10.0 g; 74.6 mmol), 2,2-dimethoxyethane (9.01 g; 86.5 mmol) and p-toluenesulfonic acid monohydrate (0.369 g; 1.94 mmol) were dissolved in tetrahydrofuran (125 mL). The clear solution was stirred at ambient temperature for 24 h. TLC (stained with ammonium molybdate) confirmed near quantitative conversion of the starting triol. The reaction was neutralised with triethylamine (10 mL) and all volatiles were removed in vacuo. Colourless oily residue was passed through a silicagel column (eluent ethyl acetate/cyclohexane 1:1). The eluent was evaporated to provide (5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methanol (12.34 g; 95% yield) as a colourless oil.

Workup

  1. customall volatiles were removed in vacuo
  2. customThe eluent was evaporated

Sources & evidence

ORD record
ord-36b3516933c442f9b5823fb96a670468
Source dataset
uspto-grants-2016_03
Patent number
US09296835B2

Linked notes

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