Benzoyl chloride → 6-Chloro-3-methylflavone-8-carboxylic acid
Reaction equation
C([O-])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[Cl:11][C:12]1[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[C:15]([OH:21])=[C:14]([C:22](=[O:25])[CH2:23][CH3:24])[CH:13]=1.[C:26](Cl)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[C:16]([C:17]([OH:19])=[O:18])[CH:20]=1)[O:21][C:24]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:23]([CH3:26])[C:22]2=[O:25]Participants
Procedure
A 47.5 g (0.33 mole) quantity of sodium benzoate was added with stirring to a mixture of 22.9 g (0.10 mole) of 5-chloro-3-propionylsalicylic acid and 42.1 g (0.30 mole) of benzoyl chloride. The reaction mixture was heated at 180° to 190° C. in an oil bath for 8 hours and was cooled. Thereto was added a 5% aqueous solution of sodium carbonate to dissolve the reaction mixture therein. The insolubles were filtered off. The solution was acidified with dilute hydrochloric acid and the separated white crystals were filtered off. The crystals were washed with an aqueous solution of alcohol and dried to obtain 28.6 g (90.9%) of white powder which had a melting point of 309° to 312° C. (sublimation). The compound thus obtained was subjected to chemical analysis with the results shown in Table 1 given below.
Workup
- temperatureThe reaction mixture was heated at 180° to 190° C. in an oil bath for 8 hours
- temperaturewas cooled
- dissolutionto dissolve the reaction mixture
- filtrationThe insolubles were filtered off
- filtrationthe separated white crystals were filtered off
- washThe crystals were washed with an aqueous solution of alcohol
- customdried
Sources & evidence
- ORD record
- ord-c77b46442f634fc0933b4710a460c947
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04634768
Reaction notes
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