HCID 21450069, compound → HCID 54394160, compound

HRID 596550Notes

Reaction equation

HRID 596550 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]1([CH2:10][CH2:11][CH:12]([CH3:15])[CH:13]=[CH2:14])[OH:9].CC(C)([O-])C.[K+]>C1C2C(CCCC2)CCC1.C(OCC)C>[CH3:15][CH:12]1[CH2:11][CH2:10][C:3]2([OH:9])[C:2]([CH3:16])([CH3:1])[CH:7]3[CH:6]=[CH:5][C:4]2([CH3:8])[CH:13]1[CH2:14]3

Participants

5

Reactant 2

HCID 21450069HCID 21450069, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54394160HCID 54394160, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7044DecalinSolvent

Procedure

0.500 g of a mixture containing equivalent amounts of the two diasteroisomers of 2,2,6-trimethyl-1-[3-methyl-pent-4-en-1-yl]-cyclohexa-3,5-dien-1-ol, obtained as indicated hereinbelow, and 0.025 g of potassium ter-butoxide in 8 ml of decaline were heated in an inert gas atmosphere in a sealed tube at 280° for 24 h. The reaction mixture was then diluted with diethyl ether, washed with water, dried over K2CO3 and finally concentrated. By bulb distillation 0.285 g of a fraction having B.p. 80°-100° /0.01 Torr were obtained. Pure 4,8,11,11-tetramethyltricyclo[5.3.1.03,8 ]undec-9-en-7-ol was isolated from the said fraction by vapour phase chromatography by means of a 5 % silicon column, of 5 mm x 2.5 m, at 190° . The yield of the final product, calculated on the amount used of the diastereomeric mixture of the starting alcohols, was of about 30 %.

Workup

  1. customobtained
  2. washwashed with water
  3. dry with materialdried over K2CO3
  4. concentrationfinally concentrated
  5. distillationBy bulb distillation 0.285 g of a fraction
  6. customwere obtained

Sources & evidence

ORD record
ord-e1628400f3a9445fab1bf630271c8ac0
Source dataset
uspto-grants-1977_03
Patent number
US04011269

Reaction notes

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