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[OH-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=1[O:13]C)[CH:4]=[CH2:5]>CS(C)=O>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:11][C:12]=1[OH:13])[CH:4]=[CH2:5]참가 물질
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- 온도
- 65 °C
실험 절차
To one liter of dimethyl sulfoxide was added 750 mL of 2 N aqueous sodium hydroxide and the mixture was heated to 65° C. The pale yellow solid 3-allyloxy-4-methoxynitrobenzene prepared above was added in portions over a 30-minute period and then the temperature was raised to 95° C. and maintained for 3 hours, after which time the starting material had been consumed. The mixture was allowed to cool and poured into a mixture of 1 L ice and 1 L 2 N HCl. 73 Grams of crude but homogeneous (by tlc 1:1 CH2Cl2/hexane) desired product was isolated as a light brown solid by filtration. This material was subsequently dissolved in 1:1 hexane/methylene chloride and filtered through silica gel to give 68 g of pale yellow solid, which, when recrystallized from ethyl/acetate/hexane, gave m.p. 61-62° C. The aqueous mother liquors from the initial crystallization above were extracted with 2 L of ethyl acetate. This was dried over sodium sulfate, filtered, and evaporated to a dark oil. Column chromatography on silica with 1:1 CH2Cl2/hexane gave an additional 12 g of the title compound as a yellow solid. Elution with 2% MeOH in CHCl3 gave 12 g of a dark oil that slowly crystallized in vacuum. This proved to be the Claisen product, 3-allyl-4-nitrocatechol.
후처리
- additionabove was added in portions over a 30-minute period
- temperaturethe temperature was raised to 95° C.
- temperaturemaintained for 3 hours
- customafter which time the starting material had been consumed
- temperatureto cool
- additionpoured into a mixture of 1 L ice and 1 L 2 N HCl
출처 및 근거
- ORD 기록
- ord-b99c1866b341431c8d9ba7ec3c3664a9
- 출처 데이터셋
- uspto-grants-2008_09
- 특허 번호
- US07419986B2
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