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

HRID 1380713노트

반응식

HRID 1380713 반응식
[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

참가 물질

6

반응물 3

HCID 962WaterHCID 895551,5-Dimethylbicyclo(3.2.1)octan-8-oneHCID 178418348HCID 178418348, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8254Dimethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f7ec33d4863f4c6791084f24050f656b
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04582945

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