Hydrochloric Acid → 4-(2-Methoxyphenyl)-3-methylbenzoic acid

HRID 639265Notes

Reaction equation

HRID 639265 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[C:7]([CH3:19])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=1[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67528780Methyl 2'-methoxy-2-methylbiphenyl-4-carboxylate

Product 1

HCID 219477594-(2-Methoxyphenyl)-3-methylbenzoic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (2-methyl-2′-methoxy-[1,1′-biphenyl]-4yl)carboxylic acid methyl ester of Step A (1.9 g, 7.4 mmol) was dissolved in tetrahydrofuran (30 mL) and 1 N sodium hydroxide (15 mL, 15 mmol) was added. The reaction mixture was heated at reflux overnight, then cooled and acidified with 2 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.6 g of product as a white solid, m.p. 160-162° C. MS [(−) APCI, m/z]: 241 [M−H]−. Anal. Calcd. for C15H14O3: C, 74.36; H, 5.82. Found: C, 73.93; H, 5.71.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01d4b7166c35412394097230109021c1
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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