Hydrochloric Acid → HCID 13450758, compound

HRID 1501022Notes

Reaction equation

HRID 1501022 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59644986HCID 59644986, compound

Product 1

HCID 13450758HCID 13450758, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 2-methoxy-4-phenoxybenzoate (1.3 g, 5 mmol), lithium hydroxide monohydrate (571 mg, 13.6 mmol), tetrahydrofuran (150 mL), methanol (50 mL) and water (50 mL) was stirred at 20° C. for 4 hours. The mixture was adjusted 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 2-methoxy-4-phenoxybenzoic acid (1 g, 82%).

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-133867f3d29c428a81bcb326890aeabe
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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