HCID 23325917, compound → Bicyclo[3.2.1]octan-8-ol, 8-ethyl-1,5-dimethyl-

HRID 1380712Notes

Reaction equation

HRID 1380712 reaction equation
[CH3:1][C:2]12[C:9]([C:11]#[CH:12])([OH:10])[C:6]([CH3:13])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[H][H]>[Ni]>[CH3:13][C:6]12[C:9]([CH2:11][CH3:12])([OH:10])[C:2]([CH3:1])([CH2:8][CH2:7]1)[CH2:3][CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 23325917HCID 23325917, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 163418Bicyclo[3.2.1]octan-8-ol, 8-ethyl-1,5-dimethyl-Yield 85%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 178 g (1 mole) 5 in 1000 ml destilled methanole was mixed with 1 g Raney nickel and hydrogenated in an autoclave (20 bar/20° to 30° C.). After about 4 h the uptake of hydrogen was finished (2 equivalents H2). The reaction mixture was taken from the autoclave, filtered, evaporated and distilled. This resulted in 155 g (85%) of 7 in form of a colorless oil having a boiling point (1 mm) of 68° C. IR: 3500/3600 cm-1 (O--H).--NMR (CCl4): δ=0.88, s (1-, 5-CH2), 0.97, t, J=7 Hz (--CH2 --CH3), 1.45 ppm, br.s (6-, 7-CH2).--MS: m/e (%)=153 (100, M+ -29), 135 (56), 125 (20), 123 (20), 107 (71), 99 (20), 95 (45), 69 (46).C12H22O (M=182.30).

Workup

  1. customhydrogenated in an autoclave (20 bar/20° to 30° C.)
  2. filtrationfiltered
  3. customevaporated
  4. distillationdistilled

Sources & evidence

ORD record
ord-8028835653f240d48959d6a7019f4be5
Source dataset
uspto-grants-1986_04
Patent number
US04582945

Reaction notes

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