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

HRID 1380713ノート

反応式

HRID 1380713 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 895551,5-Dimethylbicyclo(3.2.1)octan-8-oneHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8254Dimethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f7ec33d4863f4c6791084f24050f656b
出典データセット
uspto-grants-1986_04
特許番号
US04582945

反応ノート

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