Acetic Acid → HCID 178511239, compound
Reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]#[N:21])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1.C(O)(=O)C.O1CCOCC1>O>[C:20]([C@H:17]1[CH2:16][CH2:15][C@H:14]([C@H:11]2[CH2:12][CH2:13][C@H:8]([CH2:7][CH2:6][CH:2]=[O:1])[CH2:9][CH2:10]2)[CH2:19][CH2:18]1)#[N:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3.0 g of crude trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]cyclohexanecarbonitrile were suspended in 50 ml of water, 25 ml of glacial acetic acid and 10 ml of dioxan while gassing with argon and stirred at 100° C. for 1 hour. Thereafter, the reaction solution was treated with 100 ml of water. The aqueous phase was separated and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed with 100 ml of dilute sodium hydrogen carbonate solution and with 100 ml of water, dried over magnesium sulfate, filtered and concentrated. Recrystallization of the yellow crystals obtained (2.25 g) from 60 ml of hexane gave 1.98 g of 3-[trans-4-(trans-4-cyanocyclohexyl)cyclohexyl]propionaldehyde as colorless crystals.
Workup
- customThe aqueous phase was separated
- extractionextracted three times with 100 ml of diethyl ether each time
- washThe organic phases were washed with 100 ml of dilute sodium hydrogen carbonate solution and with 100 ml of water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customRecrystallization of the yellow crystals
- customobtained (2.25 g) from 60 ml of hexane
Sources & evidence
- ORD record
- ord-4d8f5bdf8f864c429feebd56e4dddd7b
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05013477
Reaction notes
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