Benzoic Acid → HCID 20536342, compound

HRID 1155986Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13]CC)[C:7]([OH:9])=[O:8])[CH3:2].S(=O)(=O)(O)O.O=[CH:22][C:23]([Cl:26])([Cl:25])[Cl:24].C(O)(=O)C1C=CC=CC=1>O>[OH:13][C:12]1[CH:11]=[C:10]2[C:6](=[CH:5][C:4]=1[O:3][CH2:1][CH3:2])[C:7](=[O:8])[O:9][CH:22]2[C:23]([Cl:26])([Cl:25])[Cl:24]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 16.8 g (80 mmoles) of 3,4-diethoxybenzoic acid in 100 ml. of concentrated sulfuric acid were added dropwise over thirty minutes 16 g (110 mmoles) of chloral. The reaction mixture was stirred at 25° C. for twelve hours. Thin layer chromatographic analysis indicated two components, one of which appeared to be the starting benzoic acid. Six grams of chloral were added to the reaction mixture and stirring was continued for two hours. An additional 10 g of chloral were added and the mixture was stirred for another twelve hours. The reaction mixture was then added to 50 g of ice and 50 g of water, and a solid precipitate formed. The solid product was collected by filtration and then crystallized from ethyl acetate to give 3.3 g of white crystals having a melting point above 260° C. The crystals were dissolved in ethanol and the precipitate which formed was collected, m.p. 143°-144° C. 150 mg. NMR and analysis were consistent for a structure representing 5-hydroxy-6-ethoxy-3-(trichloromethyl)phthalide.

Workup

stirringstirring
stirringthe mixture was stirred for another twelve hours
customa solid precipitate formed
filtrationThe solid product was collected by filtration
customcrystallized from ethyl acetate

Sources & evidence

ORD record: ord-8b802153bcab49a9973b887220a74f7b
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04333923

Reaction notes

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