Hydrochloric Acid → 3-Bromo-6-methoxy-2-methylbenzoic acid

HRID 582369

Reaction equation

HRID 582369 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:12]=1[CH3:13])[C:7]([O:9]CC)=[O:8].C(O)C.[OH-].[Na+].Cl>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:12]=1[CH3:13])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 11022052Ethyl 3-bromo-6-methoxy-2-methylbenzoate

Product 1

HCID 27529923-Bromo-6-methoxy-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6A (9.8 g, 34.1 mmol), water (40 ml), ethanol (80 ml) and sodium hydroxide (2.7 g, 68.3 mmol) is heated under reflux with stirring for 42 hours. The reaction mixture is diluted with water (80 ml), acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic phase is separated and concentrated. The solid material is collected by filtration, washed with water and dried yielding off-white crystals, 5.4 g (61%), mp 81-83° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. extractionextracted with dichloromethane
  4. customThe organic phase is separated
  5. concentrationconcentrated
  6. filtrationThe solid material is collected by filtration
  7. washwashed with water
  8. customdried
  9. customyielding off-white crystals, 5.4 g (61%), mp 81-83° C.

Sources & evidence

ORD record
ord-0fe5cc555f6341b987ceb98e939ad95e
Source dataset
uspto-grants-1999_07
Patent number
US05922905

Linked notes

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