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Hydrochloric Acid → N-(2-Hydroxy-4-octyloxy-phenyl)-2,2,2-trifluoro-acetamide

HRID 18447
Notes
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Reaction equation

HRID 18447 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl>CN(C=O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 18454996N-(2,4-dihydroxyphenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 58685869N-(2-Hydroxy-4-octyloxy-phenyl)-2,2,2-trifluoro-acetamideYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of N-(2,4-dihydroxy phenyl)-2,2,2-trifluoro-acetamide (0.44 g; 2 mmol) in DMF (4 mL) was added K2CO3 and 1-bromooctane (0.37 mL; 2.1 mmol). The slurry was stirred for 2 days at room temperature, poured onto 0.1 M HCl (aq.; 50 mL) and then extracted with diethylether (30 mL). The organic phase was dried (MgSO4), filtered and the eluate evaporated to leave 550 mg of black solid which was purified by chromatography (SiO2; PE80-100° C./EtOAc=4:1) to leave 100 mg (15%) of a pure white solid. Mp. 114-116° C.; MS (GC-MS; Cl): 334 (MH+).

Workup

  1. extractionextracted with diethylether (30 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe eluate evaporated

Sources & evidence

ORD record
ord-4ee9517eb9ec420cb4980422cdb446dd
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741352B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes