Water → Bicyclo[3.2.1]octan-8-ol, 1,5,8-trimethyl-

HRID 1380713Notes

Reaction equation

HRID 1380713 reaction equation
[CH3:1][C:2]12[C:9](=[O:10])[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[CH3:12][Li].O>COC.C(OCC)C>[CH3:11][C:6]12[C:9]([CH3:12])([OH:10])[C:2]([CH3:1])([CH2:8][CH2:7]1)[CH2:3][CH2:4][CH2:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 895551,5-Dimethylbicyclo[3.2.1]octan-8-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 163417Bicyclo[3.2.1]octan-8-ol, 1,5,8-trimethyl-Yield 73.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8254Dimethyl EtherSolvent

Procedure

To a solution of 45,8 g (0,3 mole) of 1,5-dimethyl-bicyclo[3.2.1]octane-8-one in 150 ml dried dimethylether at boiling temperature 250 ml (178 g) of a 5% solution of methyl lithium (4 mole) in diethylether were dropwise added under stirring. After 1 h of stirring at boiling temperature about 50 ml water were dripped in followed by extraction with diethylether. The combined organic phases were dried over Na2SO4, evaporated under vacuum and distilled which resulted in 37 g (73%) of 8 in form of a colorless oil having a boiling point (1 mm) of 74° C. IR (as oil film): 3500 cm-1 (O--H).--NMR (CCl4): δ=0,87, s, 6H (1,5-CH3), 1,05, s, 3H (8-CH3) 1.5 ppm, br.s, 4H (6,7-CH2).--MS: m/e (%)=168 (33, M+), 153 (28), 150 (29). 135 (46), 125 (30), 124 (18), 123 (31, 122 (20), 121 (42), 111 (11), 110 (10), 109 (16), 108 (19), 107 (85), . . . , 43 (100).C11H20O (M=168,27).

Workup

  1. extractionin followed by extraction with diethylether
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated under vacuum
  4. distillationdistilled which

Sources & evidence

ORD record
ord-f7ec33d4863f4c6791084f24050f656b
Source dataset
uspto-grants-1986_04
Patent number
US04582945

Reaction notes

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