Benzene → (2-Phenyl-1,3-dioxan-5-yl)methanol

HRID 1816355Notes

Reaction equation

HRID 1816355 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].C1C=CC=CC=1.C[C:15]1(C)[C:19]2(CS(O)(=O)=O)[C:20]([CH2:22][CH:16]1[CH2:17][CH2:18]2)=O.C(N(CC)CC)C>CN(C=O)C.O>[C:16]1([CH:15]2[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]2)[CH:22]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 78432Trimethylolmethane

Product 1

HCID 10679342(2-Phenyl-1,3-dioxan-5-yl)methanolYield 411.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(hydroxymethyl)-1,3-propanediol (3.0 g) and dimethoxymethyl)benzene (6.36 ml) in DMF (50 ml) was added D-10-camphorsulfonic acid (1.31 g), and the mixture was stirred at ambient temperature overnight. To a reaction mixture were added triethylamine (1.18 ml) and water (150 ml) and the solution was extracted twice with ethyl acetate (150 ml). The extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give (2-phenyl-1,3-dioxan-5-yl)methanol (4.51 g).

Workup

  1. extractionthe solution was extracted twice with ethyl acetate (150 ml)
  2. washThe extracts were washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (200 ml)
  6. washeluting with a mixture of hexane and ethyl acetate (1:1 v/v)
  7. additionThe fractions containing the object compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-53da05ec723f4f9c863a0db6e7815341
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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