4-Hydroxybenzoic Acid → Benzoic acid, 4-hexyl-, 4-carboxyphenyl ester
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O[C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)CCCCC.[CH2:33](OCC)C>>[CH2:12]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[O:29])=[CH:26][CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:33]Participants
5
Procedure
1.38 g. of 4-hydroxybenzoic acid is dissolved in 50 cc. of pyridine and mixed at -10° dropwise with a solution of 2.4 g. of 4-hexyloxybenzoic acid chloride in 10 cc. of diethyl ether. The reaction mixture is refluxed for 4 hours, the solvents are distilled off, the remainder is taken up in 50 cc. of ether, and shaken neutral with dilute hydrochloric acid and then with water. After drying, the ether is removed by evaporation, the solid residue is dissolved in chloroform, mixed with a few drops of ether, and filtered over kieselguhr. Thereafter, by fractional crystallization, with the addition of 6 cc. of ethanol, 4-(4-hexylbenzoyloxy)-benzoic acid is obtained, which is recrystallized from ethanol, m.p. 162°, t.p. 235°.
Workup
- temperatureThe reaction mixture is refluxed for 4 hours
- distillationthe solvents are distilled off
- customAfter drying
- customthe ether is removed by evaporation
- dissolutionthe solid residue is dissolved in chloroform
- additionmixed with a few drops of ether
- filtrationfiltered over kieselguhr
- customThereafter, by fractional crystallization
- additionwith the addition of 6 cc
Sources & evidence
- ORD record
- ord-dc625b4680cf48519f8c1340ead01079
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03953491
Reaction notes
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