Tetralin → 7-Allyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051414Notes

Reaction equation

HRID 2051414 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:19])=[C:9]2[C:17]=1[C:16](=[O:18])[CH:15]1[CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]1)C=C.[CH2:20]1[C:29]2C(=CC=CC=2)CC[CH2:21]1>>[CH2:29]([C:6]1[C:5]([OH:4])=[C:17]2[C:9]([CH:10]3[CH:15]([C:16]2=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11]3)=[C:8]([CH3:19])[CH:7]=1)[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 8404TetralinHCID 151571908-Allyloxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151571937-Allyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Procedure

A solution prepared by dissolving 16.7 g of 8-allyloxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 70 ml of tetralin was refluxed under heating for 10 hours. Tetralin was distilled off under reduced pressure and then the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) to obtain 12.63 g of 7-allyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone.

Workup

  1. customA solution prepared
  2. temperaturewas refluxed
  3. temperatureunder heating for 10 hours
  4. distillationTetralin was distilled off under reduced pressure
  5. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-b140748f710541658ea1a4d639abff90
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…