Red-Al → HCID 66974041, compound
Reaction equation
[CH2:1]([C:4]1([CH3:14])[CH:10]2[CH2:11][C:7]([CH3:12])([CH2:8][CH2:9]2)[CH2:6][C:5]1=[O:13])[CH:2]=[CH2:3].COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C:4]1([CH3:14])[CH:10]2[CH2:11][C:7]([CH3:12])([CH2:8][CH2:9]2)[CH2:6][CH:5]1[OH:13])[CH:2]=[CH2:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
4-Allyl-1,4-dimethyl-bicyclo[3.2.1]octan-3-one (288 g, 1.5 mol, obtained as above in EXAMPLE IV) was added to a solution of Red-Al (65%, 506 g, 1.5 mol) in toluene at 75° C. The reaction mixture was aged for 3 hours while the temperature was maintained at 75° C., then cooled to room temperature, and subsequently quenched with a solution of sodium bicarbonate (NaHCO3). Distillation of the organic layer provided 4-allyl-1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (288 g, 1.5 mol), which was then added to a MSA solution (30 g) in toluene (500 mL) and heated to reflux for 3 hours. The reaction mixture was subsequently washed with a Na2CO3 solution. Fractional distillation of the organic layer provided 2,4,8-trimethyl-5-oxa-tricyclo[6.2.1.0*2,6*]undecane (170 g) having a boiling point of 62° C. at a pressure of 0.3 mmHg.
Workup
- temperaturecooled to room temperature
- customsubsequently quenched with a solution of sodium bicarbonate (NaHCO3)
- distillationDistillation of the organic layer
Sources & evidence
- ORD record
- ord-d20554061a75453fb8917ea9372b4876
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399522B2
Reaction notes
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