Hydrochloric Acid → 4-Chloro-3-hydroxy-2-methylbenzoic acid

HRID 375747Notes

Reaction equation

HRID 375747 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Na].[Cl:13][O-].[Na+].Cl>O>[Cl:13][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH3:11])[C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2520233-Hydroxy-2-methylbenzoic AcidHCID 5360545SodiumHCID 23665760Sodium Hypochlorite

Product 1

HCID 189920604-Chloro-3-hydroxy-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2 °C

Procedure

To a suspension of 22.8 g of 3-hydroxy-2-methylbenzoic acid in 300 ml of water, cooled to 2° C., were added 55 ml of 3N sodium hydroxyde to adjust the pH to 10. To the clear solution were added within 20 minutes, at 2° to 6° C., 125 ml of 1.2N sodium hypochlorite solution, the pH being raised to 12.5. Then, 90 ml of 3N hydrochloric acid were added at once, a precipitate being formed immediately. The mixture was stirred at 0° C. for 30 minutes, and subsequently the precipitate was isolated by filtration and crystallized from diethylether/hexane to give 15.0 g of 4-chloro-3-hydroxy-2-methylbenzoic acid as white crystals of m.p. 191° C.

Workup

  1. additionTo the clear solution were added within 20 minutes, at 2° to 6° C.
  2. custombeing formed immediately
  3. customsubsequently the precipitate was isolated by filtration
  4. customcrystallized from diethylether/hexane

Sources & evidence

ORD record
ord-613cd6e2699344e4a8ad5c59f03df42f
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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