Sodium Hydroxide → HCID 14743506, compound
Reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[OH-].[CH2:16]([N+](C)(C)C)[C:17]1[CH:22]=CC=[CH:19][CH:18]=1.ClC(C)(C)C#C>O.ClCCl>[CH3:16][C:17]1([CH3:22])[CH:18]=[CH:19][C:10]2[CH:11]=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]=[CH:8][C:9]=2[O:12]1Participants
Procedure
4-Cyclopentylphenol (10.0 g), and sodium hydroxide pellets (3.7 g) were stirred in water (60 ml) and dichloromethane (60 ml). Benzyltrimethylammonium hydroxide (75 ml, 40% solution in methanol) was added to the solution, followed by 3-chloro-3-methylbutyne (12.63 g) and the reaction mixture stirred under retlux condenser, with sonication. The layers were separated, and the aqueous phase extracted with chloroform. The combined organic layers were evaporated, and the residue taken up in ether. The ether solution was washed with 10% sodium hydroxide solution, and brine and dried over anhydrous magnesium sulphate. Filtration and evaporation gave a pale brown oil (10.89 g) which was refluxed in o-dichlorobenzene (22 ml) under nitrogen for 2 h. Evaporation and chromatography of the resulting brown oil (9.3 g) gave the title benzopyran (4.18 g).
Workup
- customThe layers were separated
- extractionthe aqueous phase extracted with chloroform
- customThe combined organic layers were evaporated
- washThe ether solution was washed with 10% sodium hydroxide solution, and brine
- dry with materialdried over anhydrous magnesium sulphate
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-49b6dd57d5fb40748c6e37f1e1be2c1f
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05075460
Reaction notes
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