Ethylene Glycol → 1-(4-Benzyloxyphenyl) propan-2-one ethylene ketal

HRID 1758989Notes

Reaction equation

HRID 1758989 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:20]1[O:21][C:16]([CH3:17])([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[O:18][CH2:19]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 5612534-Benzyloxyphenylacetone

Product 1

HCID 570683201-(4-Benzyloxyphenyl) propan-2-one ethylene ketal

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-(4-benzyloxyphenyl) propan-2-one (5 g), ethylene glycol (1.4 g) and a trace amount of 4-toluenesulphonic acid, in benzene (100 ml) was heated under reflux with azetropic removal of water for 2 hours. The solvent was evaporated, the residue dissolved in ethyl acetate, washed with 1.2 N sodium bicarbonate solution, dried (MgSO4) and evaporated to give a light brown oil which crystallised on standing (6.1 g) m.p. 58°-62°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with 1.2 N sodium bicarbonate solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a light brown oil which
  7. customcrystallised

Sources & evidence

ORD record
ord-289a7d14c7934381a21f44847943727d
Source dataset
uspto-grants-1982_07
Patent number
US04338333

Reaction notes

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