Sodium Hydroxide → 3-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-ol

HRID 329475Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]([CH3:21])([CH3:20])[CH2:10][CH2:11][CH:12]1[CH2:17][C:16]([CH3:18])=[CH:15][C:14](=[O:19])[CH2:13]1.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]([CH3:21])([CH3:20])[CH2:10][CH2:11][CH:12]1[CH2:17][C:16]([CH3:18])=[CH:15][CH:14]([OH:19])[CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (0.1 g, 0.0024 mol) in tetrahydrofuran (5 mL) cooled to 0° C. was added 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one (1.0 g, 0.0048 mol) in tetrahydrofuran (5 mL). The mixture warmed on standing 16 hours and was treated with 10% sodium hydroxide solution. Subsequent workup yielded 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-ol as a mixture of two diastereoisomers (ratio: 6.5:93.5, 0.853 g). This material was determined to possess green, woody notes. NMR(CDCl3)δ0.8-1.1(m,2H), 1.2(s,6H), 1.3-1.6(m,5H), 1.7(s,1H), 1.9-2.2(m,5H), 3.2(s,3H), 4.2(brs,1H), 5.4(s,1H); IR(neat) 3400, 2975, 2925, 1670, 1380, 1360, 1090 cm-1 ; MS(m/e) 43, 73, 91, 106, 124, 147, 162, 180, 194.

Workup

temperatureThe mixture warmed

Sources & evidence

ORD record: ord-0f952b995d0c44afb1bea590263eb759
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04891447

Reaction notes

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