Hydrochloric Acid → HCID 89580617, compound

HRID 1501134Notes

Reaction equation

HRID 1501134 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])[C:5]([O:7]C)=[O:6].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89581339HCID 89581339, compound

Product 1

HCID 89580617HCID 89580617, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 3-methyl-4-(1-phenoxyethyl)benzoate (0.12 g, 0.44 mmol), lithium hydroxide monohydrate (285 mg, 6.8 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 3-methyl-4-(1-phenoxyethyl)benzoic acid (95 mg, 84%).

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-b8f1e4ad8ea441ecbfa33fab0db939c8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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