Hydrochloric Acid → HCID 89580720, compound

HRID 1501213Notes

Reaction equation

HRID 1501213 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH3:9])=[CH:5][CH:4]=1)#[N:2].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:8]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)[CH3:9])=[CH:20][CH:21]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89581116HCID 89581116, compound

Product 1

HCID 89580720HCID 89580720, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(1-(4-cyanophenoxy)ethyl)benzoate (370 mg, 1.3 mmol), lithium hydroxide monohydrate (571 mg, 13.6 mmol), tetrahydrofuran (45 mL), methanol (15 mL) and water (15 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 (55 mL×3). The combined organic phase was dried by sodium sulfate, then filtered. The filtrate was evaporated in vacuo to give 4-(1-(4-cyanophenoxy)ethyl)benzoic acid (310 mg, 74%) as a white solid. LRMS (M+H+) m/z: cald 267.09. found 267.

Workup

  1. extractionextracted with ethyl acetate (55 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1aa22655f8fb4d5e8ac97d80357f8add
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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