Hydrochloric Acid → 2-Chloro-4-methoxybenzoic acid

HRID 1824782Notes

Reaction equation

HRID 1824782 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[Cl:12].[Li+].[OH-].Cl>C1COCC1.CO.O.O>[Cl:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:13])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13498831Methyl 2-chloro-4-methoxybenzoate

Product 1

HCID 126480262-Chloro-4-methoxybenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To 2-chloro-4-methoxy-benzoic acid methyl ester (1.1 g) in THF/MeOH/water (12 mL/3 mL/3 mL) at room temperature was added LiOH (461 mg) dissolved in water. After 2 h, the reaction mixture was adjusted to pH 4 with 1N HCl and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over MgSO4. Trituration of the resulting solid in ether afforded 1.0 g (98%) of the title compound. MS: 187 (MH+), HPLC tR: 2.04 min.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-26a99f5957b74fffbd3045344c23b59d
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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