Chloroacetic Acid → Benzoic acid, 2-(carboxymethoxy)-

HRID 1362364

Reaction equation

HRID 1362364 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[Na+].Cl[CH2:14][C:15]([OH:17])=[O:16]>O>[C:15]([CH2:14][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 338Salicylic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 69461Benzoic acid, 2-(carboxymethoxy)-Yield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of salicylic acid (20 g, 145 mmol) in water (200 mL) is added carefully sodium hydroxide (60 g, 1.45 mol) followed by chloroacetic acid (27 g, 290 mmol). The mixture is refluxed for 5 d, cooled to room temperature and the precipitate is filtered and dried. Trituration with hexanes yielded the title compound (6.84 g, 24%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.66 (dd, 1H, J=8.0, 2.0 Hz), 7.45-7.47 (dd, 1H, J=8.0, 2.0 Hz), 6.97-7.05 (m, 2H), 4.77 (s, 2H).

Workup

  1. temperatureThe mixture is refluxed for 5 d
  2. filtrationthe precipitate is filtered
  3. customdried

Sources & evidence

ORD record
ord-cb4210f1881b46afa449d7d980a42260
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Linked notes

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