p-Toluenesulfonic acid → HCID 21481848, compound

HRID 1415344Notes

Reaction equation

HRID 1415344 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:14])([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15](OC(OCC)C)[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH2:1]([O:8][CH2:9][C:10]1([CH3:14])[CH2:11][O:12][CH:15]([CH3:16])[O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7765AcetalHCID 561596HCID 561596, compound

Product 1

HCID 21481848HCID 21481848, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Benzyloxy-2-methylpropane-1,2-diol (5.0g), 1,1-diethoxyethane (3.0g) and p-toluenesulphonic acid were heated at 110°-115° C with stirring until no more alcohol was evolved. The mixture was then heated at 140°-145° C for 15 minutes. After cooling, the mixture was dissolved in ether and the resulting solution was then washed with 5% potassium carbonate solution followed by water. The solution was dried over anhydrous magnesium sulphate and the solvent was removed under reduced pressure to yield a liquid which on distillation gave the desired product having a b.p. 81°-82° C at 0.3 mm Hg.

Workup

  1. temperatureThe mixture was then heated at 140°-145° C for 15 minutes
  2. temperatureAfter cooling
  3. washthe resulting solution was then washed with 5% potassium carbonate solution
  4. dry with materialThe solution was dried over anhydrous magnesium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customto yield a liquid which
  7. distillationon distillation

Sources & evidence

ORD record
ord-940f615aa68d4e07aff405dfd494fde3
Source dataset
uspto-grants-1977_01
Patent number
US04004911

Reaction notes

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