p-Toluenesulfonic acid → 5-(4-(Benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxane

HRID 1619435Notes

Reaction equation

HRID 1619435 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:18][OH:19])[CH2:16][OH:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1C=CC(S(O)(=O)=O)=C[CH:26]=1>C1(C)C=CC=CC=1.CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:18][O:19][C:21]([CH3:26])([CH3:20])[O:17][CH2:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 675171722-[4-(Benzyloxy)phenyl]propane-1,3-diol

Product 1

HCID 675165485-(4-(Benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxaneYield 79.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of 2-(4-(benzyloxy)phenyl)propane-1,3-diol (2.0 gm, 0.00775 moles) in dry toluene (500 ml), dry acetone (20 ml) and PTSA (1.2 gm, 0.0062 mole) were added and the reaction mixture was stirred for 18 hours at 30° C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was washed successively with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 1.47 gm product as white solid.

Workup

  1. additionwere added
  2. additionThe reaction mixture was poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed successively with water & brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7e1cf68f8914c0f8b6da8d1aaf55d58
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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