Malonic Acid → HCID 12667864, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:17](=[O:18])[O:16][C:14](=[O:15])[C:5]2=[C:6]([CH3:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:19](O)(=O)CC(O)=O>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[C:6]([CH3:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:14](=[O:15])[O:16][C:17]2([OH:18])[CH3:19]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture consisting of 4, 6-dimethyl-5-ethoxycarbonylbenzene-1,2-dicarboxylic acid anhydride (7.8 g. mp. 80°-81°C.), malonic acid (6.5g) dried by heating at 100°C. for 10 hr, and absolute pyridine (7 ml) was heated at 80° - 85°C. for 15 hr. After cooling, 10% aqueous hydrochloric acid was added, and the mixture was extracted with chloroform. The organic layer was washed with water, and extracted with saturated aqueous sodium bicarbonate solution. The sodium bicarbonate extract was made acidic with dilute hydrochloric acid, and further extracted with ethyl acetate. The extract was dried over MgSO4, and the solvent was removed. The resulting residue was recrystallized from ether ~ n-hexane to yield 5,7-dimethyl-6-ethoxycarbonyl-3-hydroxy-3-methylphthalide (5.4g, yield 62%) melting at 118° - 120°C.
Workup
- customdried
- temperatureabsolute pyridine (7 ml) was heated at 80° - 85°C. for 15 hr
- temperatureAfter cooling
- addition10% aqueous hydrochloric acid was added
- extractionthe mixture was extracted with chloroform
- washThe organic layer was washed with water
- extractionextracted with saturated aqueous sodium bicarbonate solution
- extractionThe sodium bicarbonate extract
- extractionfurther extracted with ethyl acetate
- dry with materialThe extract was dried over MgSO4
- customthe solvent was removed
- customThe resulting residue was recrystallized from ether ~ n-hexane
Sources & evidence
- ORD record
- ord-b1f3baec87da44c483948abd6808f6ab
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03963716
Reaction notes
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