Sodium Hydroxide → trans-1-(3',4',5'-Trimethoxyphenyl)-6,7-methylenedioxy-4-tetralone-2-carboxylic acid

HRID 1112556노트

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HRID 1112556 반응식
[C:1]([C:6]1(C(OCC)=O)[CH2:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]3[O:19][CH2:18][O:17][C:11]=3[CH:12]=2)[CH:7]1[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)([O:3]CC)=[O:2].[OH-].[Na+]>CO.O>[CH3:27][O:26][C:24]1[CH:25]=[C:20]([C@@H:7]2[C:8]3[C:13](=[CH:12][C:11]4[O:17][CH2:18][O:19][C:10]=4[CH:9]=3)[C:14](=[O:16])[CH2:15][C@H:6]2[C:1]([OH:3])=[O:2])[CH:21]=[C:22]([O:30][CH3:31])[C:23]=1[O:28][CH3:29]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 127742932,2-Dicarbethoxy-1-(3',4',5'-trimethoxyphenyl)-6,7-methylenedioxy-4-tetralone

생성물 1

HCID 22805838trans-1-(3',4',5'-Trimethoxyphenyl)-6,7-methylenedioxy-4-tetralone-2-carboxylic acid수율 66.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
110 °C

실험 절차

2,2-Dicarbethoxy-1-(3',4',5'-trimethoxyphenyl)-6,7-methylenedioxy-4-tetralone (XV; R2 = ethyl) (45 mg) was suspended in 10 ml of methanol. Aqueous NaOH (10 ml of 5%) was added and the mixture was refluxed for 3.5 hr. Then the mixture was cooled, diluted with water and washed one time with ether. The base layer was acidified to pH 2 with dilute sulfuric acid and extracted four times with chloroform. The organic layer was washed twice with water and once with saturated brine, and was dried over sodium sulfate. Filtration and evaporation gave a white solid which was heated briefly at 110° C. under nitrogen. Recrystallization of the white solid from methanol gave 24 mg (66%) of the title product, m.p. 221°-223° C.

후처리

  1. temperaturethe mixture was refluxed for 3.5 hr
  2. temperatureThen the mixture was cooled
  3. washwashed one time with ether
  4. extractionextracted four times with chloroform
  5. washThe organic layer was washed twice with water and once with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. filtrationFiltration and evaporation
  8. customgave a white solid which
  9. customRecrystallization of the white solid from methanol

출처 및 근거

ORD 기록
ord-73cf8a7b75d04300914d80b5b2c7600f
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04122092

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