Hydrochloric Acid → HCID 89581392, compound

HRID 1501064Notes

Reaction equation

HRID 1501064 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH3:8])=[CH:4][CH:3]=1.O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH3:8])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89580557HCID 89580557, compound

Product 1

HCID 89581392HCID 89581392, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(1-(4-fluorophenoxy)ethyl)benzoate (0.49 g, 1.8 mmol), lithium hydroxide monohydrate (571 mg, 13.6 mmol), tetrahydrofuran (15 mL), methanol (5 mL) and water (5 mL) was stirred at 20° C. for 4 hours. The mixture was neutralized to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo to give 4-(1-(4-fluorophenoxy)ethyl)benzoic acid (0.39 g, 83%).

Workup

  1. extractionextracted with ethyl acetate (15 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0a80ab075c904257bea0dd860eb1a399
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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