Neopentyl glycol → 2-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxane

HRID 31565

Reaction equation

HRID 31565 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:18])([CH2:16]O)[CH2:14][OH:15]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][C:13]([CH3:18])([CH3:16])[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 108989(Phenylmethoxy)acetaldehyde

Product 1

HCID 597925572-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxaneYield 96.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of benzyloxyacetaldehyde (5 g, 33.3 mmol), 2,2-dimethyl-1,3-propanediol (4.16 g, 40 mmol) and toluene (70 ml), p-toluenesulfonic acid monohydrate (287 mg, 1.51 mmol) was added and refluxed for 4 hours while removing water by the Dean-Stark apparatus. After the reaction mixture was cooled to room temperature, triethylamine (4 ml) was added to the reaction mixture and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/9) to obtain the title compound (7.6 g, yield: 96.6%) as a colorless oil.

Workup

  1. additionwas added
  2. temperaturerefluxed for 4 hours
  3. customwhile removing water by the Dean-Stark apparatus
  4. additiontriethylamine (4 ml) was added to the reaction mixture
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/9)

Sources & evidence

ORD record
ord-95876f928d594ffb87130057875b8aae
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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