Ethylene Glycol → 2-Ethylenedioxy-4a-methyl-1,2,3,4,4a,9-hexahydrophenanthrene

HRID 53872Notes

Reaction equation

HRID 53872 reaction equation
[CH3:1][C:2]12[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8][C:7]1=[CH:6][C:5](=[O:16])[CH2:4][CH2:3]2.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:17]1[CH2:18][O:19][CH:4]2[CH:5]([CH2:6][C:7]3[C:2]([CH3:1])([CH2:3]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]=3)[O:16]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6075872(3H)-Phenanthrenone, 4,4a,9,10-tetrahydro-4a-methyl-

Product 1

HCID 677259472-Ethylenedioxy-4a-methyl-1,2,3,4,4a,9-hexahydrophenanthrene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4a-methyl-4,4a,9,10-tetrahydro-2(3H)-phenanthrone 1 (7 g, 33 mmol; prepared by the method of A. L. Campbell and J. D. McChesney, Syn. Commun. 1979, 9, 471-479) is dissolved in anhydrous benzene (300 mL) and ethylene glycol (16 mL) and p-toluenesulfonic acid (0.7 g, 4 mmol) added. The solution is refluxed with the removal of water in a Dean-Stark trap according to the method of A. J. Vila, R. A. Spanevello, A. C. Olivieri, M. G. Sierra, and J. D. McChesney, Tet. Lett. 1989, 45, 4951-4960 to form the ketal, 2-ethylenedioxy-4a-methyl- 1,2,3,4,4a,9-hexahydrophenanthrene 2.

Workup

  1. customprepared by the method of A

Sources & evidence

ORD record
ord-7b385f439fe043b4ab06c8e4382889b4
Source dataset
uspto-grants-1997_04
Patent number
US05621104

Reaction notes

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