Ethylene Glycol → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

HRID 1758150Notes

Reaction equation

HRID 1758150 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@H:24]1[C@H:29]([CH2:30][CH:31]=[CH2:32])[CH2:28][CH2:27][C:26](=[O:33])[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34](O)[CH2:35][OH:36].C1(C)C=CC(S(=O)=O)=CC=1.[OH-].[Na+]>CCCCC.CCOCC.C1C=CC=CC=1>[CH2:35]1[O:36][C:26]2([CH2:27][CH2:28][C@@H:29]([CH2:30][CH:31]=[CH2:32])[C@H: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:33][CH2:34]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 13105165Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanoneHCID 178427284HCID 178427284, compound

Product 1

HCID 86738780Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

A mixture of 17.0 g. (38.1 mmoles) of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone, 47.2 g. (0.762 mole) ethylene glycol and 250 mg. of p-toluenesulfonic acid monohydride in 200 ml. of benzene was heated at reflux for 3 hours with a Dean-Stark trap. The reaction was cooled and added to 200 ml. 1 N sodium hydroxide, 100 ml. ether and 100 ml. pentane. The organic extract was washed twice with 200 ml. portions of water, twice with 200 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated (aspirator) giving a quantitative yield of the title compound.

Workup

  1. additionA mixture of 17.0 g
  2. temperatureat reflux for 3 hours with a Dean-Stark trap
  3. temperatureThe reaction was cooled
  4. additionadded to 200 ml
  5. extractionThe organic extract
  6. washwas washed twice with 200 ml
  7. dry with materialportions of saturated sodium chloride, dried over magnesium sulfate
  8. customevaporated (aspirator)

Sources & evidence

ORD record
ord-ab64f69e983c44b3a8ad03387608efe0
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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