Water → 3-Acetamido-6-(4-methoxyphenoxymethyl)benzoic acid

HRID 322232

Reaction equation

HRID 322232 reaction equation
[O-:1][C:2]1C=CC=CC=1.[Na+].[C:9]([NH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:18](=[O:19])[O:17][CH2:16]2)(=[O:11])[CH3:10].[OH2:23].[C:24]1(C)[C:25](C)=[CH:26][CH:27]=[CH:28][CH:29]=1>>[C:9]([NH:12][C:13]1[CH:14]=[C:15]([C:20]([CH2:18][O:19][C:28]2[CH:27]=[CH:26][C:25]([O:1][CH3:2])=[CH:24][CH:29]=2)=[CH:21][CH:22]=1)[C:16]([OH:23])=[O:17])(=[O:11])[CH3:10]

Participants

5

Reactant 4

HCID 962WaterHCID 7237O-XyleneHCID 5909685-Acetamido-phthalideHCID 4445035Phenolate Sodium

Product 1

HCID 220099863-Acetamido-6-(4-methoxyphenoxymethyl)benzoic acidYield 51%

Procedure

4-Methoxyphenol (1.95 g, 15.7 mmol) was allowed to react with 28% sodium methoxide (15.7 mmol) in methanol (30 ml), at room temperature for 30 minutes. After the reaction was completed, the solvent was distilled off to obtain sodium phenoxide. The obtained sodium phenoxide and 5-acetamidophthalide obtained in Reference Example 8 (3.0 g, 15.7 mmol) were heated under reflux in xylene (30 ml) for 14 hours. The reaction mixture was poured into water and washed twice with ether (30 ml). The aqueous layer was adjusted to pH 3 with 1 mol/l hydrochloric acid and the precipitated solid was separated by filtration to give 3-acetamido-6-(4-methoxyphenoxymethyl)benzoic acid (2.49 g, 51%).

Workup

  1. temperaturewere heated
  2. washwashed twice with ether (30 ml)
  3. customthe precipitated solid was separated by filtration

Sources & evidence

ORD record
ord-2a7813ac625d461e9b01ab2b7371fd53
Source dataset
uspto-grants-2001_04
Patent number
US06211227B1

Linked notes

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