Hydrochloric Acid → 2-Acetoxy-5-bromo-6-methylbenzoic acid

HRID 365956

Reaction equation

HRID 365956 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1.Cl>O.C(OCC)(=O)C>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 110534513-Bromo-6-hydroxy-2-methylbenzoic acid

Product 1

HCID 110111492-Acetoxy-5-bromo-6-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1B (6.93 g, 30 mmol), acetic anhydride (3.5 ml, 36 mmol) and pyridine (15 ml) is heated under reflux with stirring for 16 hours. The reaction mixture is diluted with water and ethyl acetate. The organic phase is acidified with dilute hydrochloric acid and washed with water twice. The organic phase is concentrated in vacuo and the residue is purified by flash chromatography (dichloromethane:methanol, 9:1 v/v) yielding the pure product as a yellow oil, 7.4 g, (90.3%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. washwashed with water twice
  4. concentrationThe organic phase is concentrated in vacuo
  5. customthe residue is purified by flash chromatography (dichloromethane:methanol, 9:1 v/v)

Sources & evidence

ORD record
ord-53b724b373e640f3b1a2566c1fdb3d86
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Linked notes

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