Hydrochloric Acid → 4-Decanoyloxy-2-fluorobenzoic acid
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>ClCCl.CN(C1C=CC=CN=1)C>[C:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]Participants
7
Procedure
15.6 Grams (0.1 mol) of 4-hydroxy-2-fluorobenzoic acid was dissolved in 140 ml of dichloromethane. To this solution were consecutively added 16 ml of triethylamine, 20.1 g (0.11 mol) of n-decanoic acid chloride and 0.97 g (0.0079 mol) of dimethylaminopyridine, and the mixture was stirred at room temperature for a whole day and night. To this was added 50 ml of 10% hydrochloric acid, and the mixture was extracted with 100 ml of ether three times. An organic layer was washed with 100 ml of a sodium chloride aqueous solution three times, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and then the residue was washed with 400 ml of hexane to give 25,5 g (yield 82%) of the intended product.
Workup
- extractionthe mixture was extracted with 100 ml of ether three times
- washAn organic layer was washed with 100 ml of a sodium chloride aqueous solution three times
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
- washthe residue was washed with 400 ml of hexane
Sources & evidence
- ORD record
- ord-5dd26ac4ee5f4a0ca6f7942174620e43
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716544
Reaction notes
Loading…