Hydrochloric Acid → Benzoic acid, 3-(1,1-dimethylethyl)-4-methoxy-

HRID 2225162Notes

Reaction equation

HRID 2225162 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].CO.O.Cl>[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 10775404Methyl 3-tert-butyl-4-methoxybenzoate2×

Product 1

HCID 10488578Benzoic acid, 3-(1,1-dimethylethyl)-4-methoxy-Yield 93.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Preparation C11, Step 2: Methyl 3-tert-butyl-4-methoxybenzoate (1.12 g, 5.03 mmol, 1 eq) was dissolved in 1N NaOH in methanol (50.38 mL, 50.3 mmol, 10 eq) at room temperature then refluxed for 4 hours. Worked up stripping off the methanol. Added H2O (10 mL) then adjusted the pH to 3 with 6N HCl. Solids precipitated. Extracted the suspension 3 times with methylene chloride (20 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give 3-tert-butyl-4-methoxybenzoic acid (0.98 g) as a white solid. Yield=93%. LCMS detects (M+H)+=208.25.

Workup

  1. customPreparation C11, Step 2
  2. temperaturethen refluxed for 4 hours
  3. customSolids precipitated
  4. extractionExtracted the suspension 3 times with methylene chloride (20 mL)
  5. dry with materialdried (sodium sulfate)

Sources & evidence

ORD record
ord-676c8974dc644a15899c6e640447caba
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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