Boron trifluoride etherate → 2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane
Reaction equation
[CH3:1][C:2]1[CH:7]([CH2:8][CH2:9][C:10]([CH3:12])=[O:11])[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=1.C(OCC)(OCC)O[CH2:17][CH3:18].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)C>[CH2:17]([O:11][C:10]1([CH3:12])[CH2:9][CH2:8][CH:7]2[C:2](=[CH2:1])[CH:3]1[CH2:4][CH2:5][C:6]2([CH3:14])[CH3:13])[CH3:18]Participants
Procedure
480 g (2.21 mol) of dihydro-α-ionone, 368 g (2.48 mol) of triethyl orthoformate and 480 ml of abs. ethanol are treated dropwise while stirring during 15 minutes with a solution of 34.5 g (0.31 mol) of boron trifluoride etherate in 500 ml of ethanol and the mixture is subsequently heated to an internal temperature of 46°-48° for 60 minutes. After cooling the reaction mixture to room temperature it is stirred with 600 ml of a 10% aqueous sodium hydroxide solution. After extraction with ether and evaporation of the organic phase there are obtained 668.7 g of a slightly yellow liquid which, after flash distillation in a vacuum, gives 480.5 g of crude product (b.p. 45°-73°, 0.07 mbar). After fractionation in a vacuum over a 20 cm Widmer column there are obtained 406.2 g (82.7% of theory) of a slightly yellowish colored liquid (b.p. 48°-67°, 0.06 mbar) which contains the desired bicyclo-nonane in an isomer ratio of exo:endo=2:1
Workup
- temperaturethe mixture is subsequently heated to an internal temperature of 46°-48° for 60 minutes
- extractionAfter extraction
- customwith ether and evaporation of the organic phase there
- customare obtained 668.7 g of a slightly yellow liquid which
- distillationafter flash distillation in a vacuum
Sources & evidence
- ORD record
- ord-9b8b3c76b67a4e78a9cef974334e19ba
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05023232
Reaction notes
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