Hydrochloric Acid → 4-Butoxybenzoic acid

HRID 497510Notes

Reaction equation

HRID 497510 reaction equation
[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CCO.O>[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12105766HCID 12105766, compound

Product 1

HCID 729714-Butoxybenzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(Scheme 1, Compound B) To a solution of ethyl 4-butoxybenzoate (2.0 g, 9.6 mmol) in EtOH (30 mL) was added NaOH (10 N, 6 mL, 60 mmol). The resulting mixture was stirred at room temperature for 3 hours, diluted with H2O (30 mL), acidified to about pH 1.0 using HCl (6N). The precipitates were filtered off by filter paper, washed by H2O and hexanes. This compound was obtained as a white solid. (1.63 g, 9.1 mmol, 94% yield). 1H NMR (DMSO-d6) δ 12.59 (br. s, 1H), 7.88 (d, 2H, J=9.5 Hz), 6.97 (d, 2H, J=9.5 Hz), 4.01 (t, 2H, J=6.5 Hz), 1.68 (m, 2H), 1.42 (m, 2H), 0.91 (t, 3H, J=6.5 Hz); 13C NMR (DMSO): 166.9, 162.2, 131.2, 122.7, 114.0, 67.3, 30.5, 18.6 and 13.5; Mass Spec.: 195.17 (MH+).

Workup

  1. filtrationThe precipitates were filtered off
  2. filtrationby filter paper
  3. washwashed by H2O and hexanes
  4. customThis compound was obtained as a white solid

Sources & evidence

ORD record
ord-f0c38745fddf4ea8801abcf712461400
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

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