Ethylene Glycol → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-3-en-1-one ethylene ketal

HRID 1758173Notes

Reaction equation

HRID 1758173 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31](O)[CH2:32][OH:33].C1(C=CC(O)=CC=1)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:32]1[O:33][C:26]2([CH2:27][CH2:28][CH:29]=[C:24]([C:10]3[CH:11]=[CH:12][C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:25]2)[O:30][CH2:31]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 785HydroquinoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enone

Product 1

HCID 572072353-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-3-en-1-one ethylene ketal

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 500 mg. of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-2-en-1-one, 7.8 g. of ethylene glycol, 375 mg. of hydroquinone and 50 mg. of p-toluenesulfonic acid monohydrate in 50 ml. of benzene is heated at reflux for 12 hours using a Dean-Stark condenser filled with 3A molcular sieves. The reaction is cooled, added to 500 ml. saturated sodium bicarbonate and the quenched mixture extracted with three 150 ml. portions of ether, dried over magnesium sulfate and evaporated to a solid. This solid is purified via column chromatography on 50 g. of silica gel eluted with 50% ether-petroleum ether to yield the title product.

Workup

  1. temperatureat reflux for 12 hours
  2. temperatureThe reaction is cooled
  3. additionadded to 500 ml
  4. extractionsaturated sodium bicarbonate and the quenched mixture extracted with three 150 ml
  5. dry with materialportions of ether, dried over magnesium sulfate
  6. customevaporated to a solid
  7. customThis solid is purified via column chromatography on 50 g
  8. washof silica gel eluted with 50% ether-petroleum ether

Sources & evidence

ORD record
ord-312819ab01c445358e15fd1bba0b14f0
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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