Methyl iodide → 3-(3-Methoxy-3-methylbutyl)-1,5-dimethylcyclohexan-1-ol

HRID 329481Notes

Reaction equation

HRID 329481 reaction equation
[CH3:1][O:2][C:3]([CH3:15])([CH3:14])[CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[CH2:7]1.[I-].[Mg].I[CH3:19].[Cl-].[NH4+]>C(OCC)C>[CH3:1][O:2][C:3]([CH3:14])([CH3:15])[CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][C:8]([CH3:19])([OH:13])[CH2:7]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 30165Iodide IonHCID 5462224MagnesiumHCID 147939943-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one

Product 1

HCID 147939983-(3-Methoxy-3-methylbutyl)-1,5-dimethylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

3-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one (5.0 g, 0.025 mol) dissolved in diethyl ether (5.0 mL) was added to a cooled (5° C.) solution of methylmagensium iodide formed by treating magnesium turnings (0.70 g, 0.028 mol) in diethyl ether (20 mL) with iodomethane (1.6 mL, 0.026 mol). After stirring 16 hours at 25° C., a saturated aqueous ammonium chloride solution (ca. 2 mL) was added and subsequent workup yielded 3-(3-methoxy-3-methylbutyl)-1,5-dimethylcyclohexan-1-ol as a mixture of diastereoisomers in a ratio of 2.9:65.6:1.9:29.6, bp0.5 147°-149° C. This compound was determined to possess a warm woody note. NMR(CDCl3)δ0.5(m,1H), 0.9(d,3H), 1.0-1.1(m,1H), 1.2(s,6H), 1.3(s,3H), 1.3-1.9(m,10H), 1.9-2.0(brs,1H), 3.2(s,3H); IR(neat) 3400, 2925, 1460, 1370, 1220, 1080 cm-1 ; MS(m/e) 43, 55, 73, 107, 122, 163, 181, 213, 214.

Workup

  1. additionwas added to
  2. customformed

Sources & evidence

ORD record
ord-734d36899e274d4e91dd0e9307e7b72d
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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