Sodium Hydroxide → 4-Butyrylbenzoic acid

HRID 2173877Notes

Reaction equation

HRID 2173877 reaction equation
[C:1]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>O1CCCC1.CO>[C:1]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23143286Methyl 4-butyrylbenzoate

Product 1

HCID 189835644-Butyrylbenzoic acidYield 65.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-butyrylbenzoate (256.1 mg, 1.242 mmol) was dissolved in tetrahydrofuran (3 mL) and methanol (3.0 mL). 1N aqueous sodium hydroxide (3.73 mL) was added and the reaction mixture was heated to 50° C. for 3 h. The reaction mixture was then cooled to room temperature and concentrated. The crude residue was taken up in water and acidified to pH 5 by addition of 1N aqueous HCl. A colorless precipitate formed. The solids were filtered off and dried under vacuum to give 4-butyrylbenzoic acid (155.4 mg, 65%) as a colorless solid. 1H NMR (400 MHz, CDCl3, δ) 8.16-8.21 (m, 2H), 8.01-8.05 (m, 2H), 2.98 (t, J=7.2 Hz, 2H), 1.78 (m, 2H), 1.01 (t, J=7.41 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. additionacidified to pH 5 by addition of 1N aqueous HCl
  4. customA colorless precipitate formed
  5. filtrationThe solids were filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a389deb9369b4464bd85623a817370e4
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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