p-Toluenesulfonic acid → 5-Benzyloxymethyl-5-cyclohexyl-2,2-dimethyl-1,3-dioxane

HRID 2372413Notes

Reaction equation

HRID 2372413 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH2:13][OH:14])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:23](OC)([CH3:25])[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]1([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:11][O:12][C:23]([CH3:25])([CH3:24])[O:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 193733732-Benzyloxymethyl-2-cyclohexylpropan-1,3-diol

Product 1

HCID 199044385-Benzyloxymethyl-5-cyclohexyl-2,2-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Benzyloxymethyl-2-cyclohexyl-propan-1,3-diol(3 g.),2,2-dimethoxypropane (8 ml), p-toluenesulphonic acid (150 mg.) and molecular sieves (type 4A) were heated in refluxing dry toluene (50 ml.) for four hours. The mixture was cooled and filtered. The filtrate was diluted with ether and the ethereal solution was extracted with aqueous sodium hydrogen carbonate solution. The ethereal solution was washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:5 ether:hexane. 5-Benzyloxymethyl-5-cyclohexyl-2,2-dimethyl-1,3-dioxane(3.0 g) was obtained as a colourless oil.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ether
  4. extractionthe ethereal solution was extracted with aqueous sodium hydrogen carbonate solution
  5. washThe ethereal solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with 1:5 ether

Sources & evidence

ORD record
ord-03da6fc1a0894c4b81b13c5694c76dda
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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