Methanol → HCID 20469266, compound

HRID 1388635Notes

Reaction equation

HRID 1388635 reaction equation
[CH3:1][C:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]([CH3:13])[CH2:5][C:4](=[O:14])[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CO>CCCCCC>[CH3:1][C:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]([CH3:13])[CH2:5][CH:4]([OH:14])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 936962-Cyclohexen-1-one, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20469266HCID 20469266, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 3,5-dimethyl-4-(3methyl-2-butenyl)-2-cyclohexen-1-one (4 g, 0.02 mol) in hexane (25 mL) was stirred under nitrogen at 0° C. and 1 M diisobutylaluminum hydride (25 mL) was added dropwise over 30 minutes. The mixture was stirred for 2 hours and methanol (60 mL) added to precipitate the salts. The solution was filtered and washed with 15% hydrochloric acid, saturated sodium bicarbonate and brine. Drying (Na2SO4), and solvent removal, followed by Kugelrohr distillation gave 3.8 g of 3,5-dimethyl-4-(3-methyl-2-butenyl)-2-cyclohexen-1-ol, bp 135° -140° C./0.5 mm.

Workup

  1. customto precipitate the salts
  2. filtrationThe solution was filtered
  3. washwashed with 15% hydrochloric acid, saturated sodium bicarbonate and brine
  4. customDrying
  5. custom(Na2SO4), and solvent removal
  6. distillationfollowed by Kugelrohr distillation

Sources & evidence

ORD record
ord-0f3cac3985d845b6b0ac4da7c2056071
Source dataset
uspto-grants-1984_02
Patent number
US04432378

Reaction notes

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