Acetone → HCID 19767493, compound

HRID 1590608Notes

Reaction equation

HRID 1590608 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)([CH2:12][OH:13])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:25][C:26]([CH3:28])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:25][C:26]1([CH3:28])[O:11][CH2:10][C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)([CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH2:12][O:13]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 19767503HCID 19767503, compound

Product 1

HCID 19767493HCID 19767493, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(3,4-Difluorophenyl)-2-(4-methoxybenzyloxymethyl)propane-1,3-diol (16.5 g, 50 mmol), acetone (7.5 ml) and p-toluene sulphonic acid (100 mg) were heated to reflux in benzene (100 ml) and water was removed using Dean and Stark apparatus. After refluxing overnight the cooled solution was washed with saturated aqueous sodium bicarbonate solution and was dried over anhydrous magnesium sulphate. Evaporation gave 2,2-dimethyl-5-(3,4-difluorophenyl)-5-(4-methoxybenzyloxymethyl)-1,3-dioxane as a yellow oil (17.7 g, 97%, Nmr δ 7.2-6.8 (7H,m), 4.4 (2H,s), 4.05 (2H,d), 3.95 (2H,d), 3.8 (3H, s), 3.7 (2H,s), 1.4 (6H,s).

Workup

  1. customwater was removed
  2. temperatureAfter refluxing overnight the cooled solution
  3. washwas washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialwas dried over anhydrous magnesium sulphate
  5. customEvaporation

Sources & evidence

ORD record
ord-47f3463bfc4c437aa5ffe8066fa43f46
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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