Hydrochloric Acid → HCID 11587019, compound

HRID 966088Notes

Reaction equation

HRID 966088 reaction equation
FC1C=CC(C[O:7][C:8](=[O:25])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:11]([F:24])[CH:10]=2)=CC=1.[OH-].[K+].Cl>O.O1CCOCC1>[F:24][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:8]([OH:25])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69039983HCID 69039983, compound

Product 1

HCID 11587019HCID 11587019, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoro-4-(4-fluoro-benzyloxy)-benzoic acid 4-fluoro-benzyl ester (8.1 g, 22 mmol) and potassium hydroxide (6.1 g, 109 mmol) in water:dioxane (4:1, 150 mL) was heated at 100° C. for 12 h. After cooling to room temperature the mixture was acidified to pH 3 with HCl and the mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts washed with brine (100 mL) and dried over sodium sulfate. Filtration and half evaporation gave a precipitate which was filtered off and crystallised from ethyl acetate:heptane to afford the title compound (4.9 g, 85%) as a white solid. MS: m/e=263.0 (M−H−).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  3. washthe combined extracts washed with brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and half evaporation
  6. customgave a precipitate which
  7. filtrationwas filtered off
  8. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0047163b53d54c8480e8ad6989fd41df
Source dataset
uspto-grants-2005_10
Patent number
US06951884B2

Reaction notes

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