Acetone → ethyl 7-[5-(4-acetyl-3-hydroxyphenoxy)pentyloxy]-4-oxo-4H-1-benzopyran-2-carboxylate
Reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[CH:3]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[I-].[K+].[CH3:26][C:27]([CH3:29])=[O:28]>>[C:27]([C:29]1[CH:6]=[CH:7][C:8]([O:9][CH2:4][CH2:3][CH2:2][CH2:17][CH2:16][O:1][C:2]2[CH:17]=[CH:16][C:5]3[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=3[CH:3]=2)=[CH:10][C:18]=1[OH:21])(=[O:28])[CH3:26]Participants
5
Procedure
A mixture of 3.05 parts of 4-(5-bromopentyloxy)-2-hydroxy acetophenone, 2.34 parts of ethyl 7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 1.38 parts of potassium carbonate and 0.5 parts of potassium iodide, in 200 parts of dry acetone, was heated under reflux for 24 hours. The solution was filtered while hot and the inorganic salts washed with hot acetone. The solvent was removed to leave a yellow solid, which was washed with water and ether. The insoluble yellow solid was crystallised from ethyl alcohol to yield 3.3 parts of ethyl 7-[5-(4-acetyl-3-hydroxyphenoxy)pentyloxy]-4-oxo-4H-1 -benzopyran-2-carboxylate as pale yellow needles, melting point 136°-137° C.
Workup
- temperatureunder reflux for 24 hours
- filtrationThe solution was filtered while hot and the inorganic salts
- washwashed with hot acetone
- customThe solvent was removed
- customto leave a yellow solid, which
- washwas washed with water and ether
- customThe insoluble yellow solid was crystallised from ethyl alcohol
Sources & evidence
- ORD record
- ord-855b84b7119545298974206c817d0b03
- Source dataset
- uspto-grants-1979_01
- Patent number
- US04133889
Reaction notes
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