Isopropanol → HCID 59438527, compound
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].[CH3:15][CH:16](O)[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH-].[Na+]>O1CCCC1>[CH:16]([O:12][C:5]1[CH:4]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([CH3:17])[CH3:15]Participants
Procedure
To a solution of p-(trifluoromethyl)salicylic acid (CAS 345-28-8) (500 mg, 2.271 mmol), 2-propanol (0.209 ml, 2.725 mmol) and triphenylphosphine (706.2 mg, 2.612 mmol) in 6.5 ml tetrahydrofurane under nitrogen at 0° C., was added dropwise a solution of di-tert-butyl azodicarboxylate (575.2 mg, 2.498 mmol) in 1 ml tetrahydrofurane. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 hours. 8 ml 2N NaOH (15.9 mmol) was added and the reaction mixture was heated in an 80° C. oil bath for 5 hours. The reaction mixture was allowed to cool to room temperature and extracted twice with 5 ml ether. The aqueous layer was acidified under ice bath cooling with a 5N HCl solution to pH 1. The resulting precipitate was filtered and dried in vacuo to provide 444 mg (79%) of the title compound as a white solid. MS (m/e): 247.0 (M+H+).
Workup
- temperaturethe reaction mixture was heated in an 80° C. oil bath for 5 hours
- temperatureto cool to room temperature
- extractionextracted twice with 5 ml ether
- temperaturecooling with a 5N HCl solution to pH 1
- filtrationThe resulting precipitate was filtered
- customdried in vacuo
Sources & evidence
- ORD record
- ord-51e9ad4bd8984e4d81275000deff9c9e
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404673B2
Reaction notes
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