Sodium Hydroxide → 4-(2-Hydroxyethoxy)benzenecarboxylic acid

HRID 552575

Reaction equation

HRID 552575 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[OH:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:14])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76670Benzoic acid, 4-(2-hydroxyethoxy)-, methyl ester

Product 1

HCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

4-(2-Hydroxy-ethoxy)-benzoic acid methyl ester (400 mg, 2.04 mmol) is combined with a mixture of 1 N NaOH (3 mL) and MeOH (3 mL) and the mixture is stirred at 80° C. for 1 h. The solvents are evaporated and the resulting residue is dissolved in a small amount of water and acidified with 1 N HCl. The crystals are collected, washed with water, and dried to provide 154 mg (42%) of the titled compound. NMR (DMSO-d6): δ 12.64 (br, 1H), 7.90 (d, 2H, J=8.2 Hz), 7.03 (d, 2H, J=8.2 Hz), 4.93 (br, 1H), 4.07 (t, 2H, J=4.9 Hz), 3.75 (m, 2H).

Workup

  1. customThe solvents are evaporated
  2. dissolutionthe resulting residue is dissolved in a small amount of water
  3. customThe crystals are collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cc91f364263a4d398dcf6d2721123312
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Linked notes

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