2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enone → 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enol

HRID 1793232Notes

Reaction equation

HRID 1793232 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:5][CH2:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][C:2]1[CH:3]([OH:14])[C:4]([CH3:13])([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:5][CH2:6][CH:7]=1

Participants

4

Reactant 2

HCID 115792582,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 220263442,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enolYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26.04 mmol) was added dropwise to a suspension of lithium aluminium hydride (0.73 g, 18.2 mmol) in diethyl ether at 0° C. The mixture was stirred at room temperature for 1 h. The resulting suspension was quenched with water, aqueous sodium hydroxide solution and again water, was then filtered and concentrated in vacuo. The residue was distilled (bp. 110° C./0.1 Torr) to yield 4.93 g (98%) of the alcohol as a mixture of 2 diastereomers. 1H-NMR (200 MHz, CDCl3): 5.49 (bs, 1H, 3-H), 5.34-5.15 (m, 1H, 2′-H), 3.57/3.44 (2d, J=4.5, 5.5 Hz, 1H, 1-H), 2.25-1.82 (m, 4H), 1.81-1.71 (m, 6H), 1.65/1.61 (2s, 3H), 1.62-1.19 (m, 3H), 0.93/0.82 (2s, 3H, 6-CH3) ppm. GC/MS (EI) isomer a: 194 (M+, 4), 176 (44), 161 (42), 125 (12), 107 (94), 84 (70), 69 (38), 55 (50), 43 (100). IR (ATR): 3365s, 2966s, 2916vs, 1450s, 1375s, 1239m, 1030m, 1007 s cm−1.

Workup

  1. customThe resulting suspension was quenched with water, aqueous sodium hydroxide solution and again water
  2. filtrationwas then filtered
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled (bp. 110° C./0.1 Torr)

Sources & evidence

ORD record
ord-8a4703e3c2844eb2a6fea95691c7e22c
Source dataset
uspto-grants-2006_07
Patent number
US07078570B2

Reaction notes

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