Methane → 2-Chloro-5-hydroxybenzoic acid

HRID 49415

Reaction equation

HRID 49415 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N([O-])=[O:13].[Na+].C>S(=O)(=O)(O)O.O>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([OH:13])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 297MethaneHCID 378795-Amino-2-chlorobenzoic acidHCID 23668193Sodium Nitrite2×

Product 1

HCID 4582102-Chloro-5-hydroxybenzoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

5-Amino-2-chlorobenzoic acid (85%, 10 g, 49.7 mmol) was suspended in diluted sulphuric acid (1.25%, 800 mL) and cooled to 5° C. on an ice bath. Sodium nitrite (5 g, 72 mmol) dissolved in water (150 mL) was added slowly while keeping the temperature of the reaction below 5° C. After addition of the sodium nitrite the reaction was stirred for another 45 min at 5-10° C. until a clear solution was obtained. The reaction mixture was poured into hot (70-85° C.) water (1.5 L), charcoal added and the reaction mixture heated at reflux for 25 min. Filtration and extraction with ethyl acetate afforded 6.7 g of the desired product as light brown crystals.

Workup

  1. additionwas added slowly
  2. customthe temperature of the reaction below 5° C
  3. customwas obtained
  4. additionadded
  5. temperaturethe reaction mixture heated
  6. temperatureat reflux for 25 min
  7. filtrationFiltration and extraction with ethyl acetate

Sources & evidence

ORD record
ord-e36e5113c886451793a725da5fffdad1
Source dataset
uspto-grants-2004_03
Patent number
US06706749B2

Linked notes

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