Methyl 4-ethyl-2-methoxybenzoate → 4-Ethyl-2-methoxybenzoic acid

HRID 1625579Notes

Reaction equation

HRID 1625579 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([O:13][CH3:14])[CH:4]=1)[CH3:2]>[OH-].[Na+]>[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:13][CH3:14])[CH:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 23551559Methyl 4-ethyl-2-methoxybenzoate

Product 1

HCID 186873494-Ethyl-2-methoxybenzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-ethyl-2-methoxybenzoate (example 18c) (2.01 g, 10.3 mmol) was suspended in 1M aq. NaOH (40 mL) and the mixture was stirred at 60° C. overnight. The reaction mixture was cooled to rt and washed with hexanes. The aqueous layer was then separated and acidified with 6N HCl to pH 2. A white precipitate was collected washed with water and dried to give 4-ethyl-2-methoxybenzoic acid (1.8 g, 97%) as a white solid. 1H NMR (300 MHz, dMSO): δ 1.16-1.20 (t, 3H), 2.60-2.65 (dd, 2H), 3.80 (s, 3H), 6.82-6.84 (d, 1H), 6.95 (s, 1H), 7.57-7.59 (d, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washwashed with hexanes
  3. customThe aqueous layer was then separated
  4. customA white precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-841e7d49cf554c5196f5e99333eea021
Source dataset
uspto-grants-2014_07
Patent number
US08784782B2

Reaction notes

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