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

HRID 1586588Notes

Reaction equation

HRID 1586588 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-7f7b09b36485488eae45d0ab56f4abaa
Source dataset
uspto-grants-1999_08
Patent number
US05945567

Reaction notes

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