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

HRID 1112556Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 110 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-73cf8a7b75d04300914d80b5b2c7600f
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04122092

Reaction notes

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