Ethanol → 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2,5-imidazolinedione
Reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](C=O)[CH:5]=[CH:4][C:3]1=2.[CH2:17]([OH:19])[CH3:18].[C-]#N.[Na+].[C:23](=[O:26])([O-])[O-].[NH4+:27].[NH4+:28]>O>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:18]3[C:17](=[O:19])[NH:28][C:23](=[O:26])[NH:27]3)[CH:5]=[CH:4][C:3]1=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
21.6 g (0.1 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthaldehyde and 350 ml of ethanol were introduced into a three-necked flask. A solution of 14.7 g (0.3 mol) of sodium cyanide and 38.4 g (0.4 mol) of ammonium carbonate in 350 ml of water was added and the mixture was heated at 50° C. for 6 hours. The reaction medium was concentrated to 300 ml by evaporation under reduced pressure and then extracted with ethyl ether. The organic phase was decanted off, washed with water, dried over magnesium sulfate and evaporated. 24.9 g (87%) of the intended compound of melting point 213°-214° C. were recovered.
Workup
- concentrationThe reaction medium was concentrated to 300 ml by evaporation under reduced pressure
- extractionextracted with ethyl ether
- customThe organic phase was decanted off
- washwashed with water
- dry with materialdried over magnesium sulfate
- customevaporated
- custom24.9 g (87%) of the intended compound of melting point 213°-214° C. were recovered
Sources & evidence
- ORD record
- ord-4af91d2dbea547929961febd59c201cf
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05709867
Reaction notes
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