Hydrochloric Acid → HCID 90314056, compound

HRID 1484177Notes

Reaction equation

HRID 1484177 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[CH:9]=[O:10])=[CH:4][CH:3]=1.P([O-])(O)(O)=[O:22].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl.[S-2].[Na+].[Na+]>CC(O)(C)C.O.C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[CH:11][C:8]=2[C:9]([OH:22])=[O:10])=[CH:4][CH:3]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 14804Sodium SulfideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 58753821HCID 58753821, compound

Product 1

HCID 90314056HCID 90314056, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(4-fluorophenoxy)-4-(trifluoromethyl)benzaldehyde (1.16 g, 4.08 mmol) in tBuOH (11.60 mL), water (7.30 mL), acetonitrile (7.30 mL) was added sodium dihydrogen phosphate (1.47 g, 12.25 mmol), 2-methyl-2-butene (2.16 mL, 20.42 mmol) and sodium chlorite (1.11 g, 12.25 mmol) and the reaction mixture was stirred at 25° C. for 2 hours. The reaction was acidified with 1N HCl and diluted with ethyl acetate. Sodium sulfide was added to remove the slightly yellow color. The 2 layers were separated and the aqueous layer extracted 2 additional times with ethyl acetate. The organics were combined, dried with MgSO4, filtered and evaporated to give 2-(4-fluorophenoxy)-4-(trifluoromethyl)benzoic acid (1.0 g, 82%) as a yellow solid that was used in the next step without further purification. 1H NMR (400 MHz, DMSO) δ 8.01 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.9 Hz, 1H), 7.33-7.18 (m, 3H), 7.14-7.01 (m, 2H) ppm.

Workup

  1. customto remove the slightly yellow color
  2. customThe 2 layers were separated
  3. extractionthe aqueous layer extracted 2 additional times with ethyl acetate
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bc65276c1a024e7c93614662e51ea996
Source dataset
uspto-grants-2016_08
Patent number
US09421196B2

Reaction notes

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