Undecane → HCID 66974041, compound
Reaction equation
CCCCCCCCCCC.[CH2:12]([C:15]1([CH3:25])[CH:21]2[CH2:22][C:18]([CH3:23])([CH2:19][CH2:20]2)[CH2:17][C:16]1=[O:24])[CH:13]=[CH2:14].COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH2:12]([C:15]1([CH3:25])[CH:21]2[CH2:22][C:18]([CH3:23])([CH2:19][CH2:20]2)[CH2:17][CH:16]1[OH:24])[CH:13]=[CH2:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Preparation of 2,4,8-Trimethyl-5-oxa-tricyclo[6.2.1.0*2,6]undecane (Structure 4): 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-fa5560a3480843a5890d2fc0df1c01a4
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357358B2
Reaction notes
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