Methanol → HCID 57660218, compound

HRID 909397Notes

Reaction equation

HRID 909397 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[OH:12].Cl.[NH2:15][OH:16].CO.C[O-].[Na+].CO>O>[OH:16][NH:15][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[OH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 21474524HCID 21474524, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 57660218HCID 57660218, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

350 g of 2-hydroxy-4-(hydroxymethyl)benzoic acid methyl ester and 160 g of hydroxylamine hydrochloride were added to 700 mL of methanol. Under heating reflux, 1.11 kg of 28% sodium methoxide/methanol solution was added dropwise, and this was stirred for 3 hours. To this, 2.1 L of water was added and 850 mL of solvent was distilled off under atmospheric pressure. Then, 196 mL of hydrochloric acid was added at 40-50° C. The result was stirred for 30 minutes at the same temperature, and 116 mL of hydrochloric acid was added dropwise. After filtering solids, 291 g of N,2-dihydroxy-4-(hydroxymethyl)benzamide was obtained in the form of a pale yellowish-white solid.

Workup

  1. temperatureUnder heating
  2. temperaturereflux
  3. distillation850 mL of solvent was distilled off under atmospheric pressure
  4. additionThen, 196 mL of hydrochloric acid was added at 40-50° C
  5. stirringThe result was stirred for 30 minutes at the same temperature, and 116 mL of hydrochloric acid
  6. additionwas added dropwise
  7. filtrationAfter filtering solids

Sources & evidence

ORD record
ord-98487779d1234c13aa7eac168e75b4ab
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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