Sodium Hydroxide → 5-Chloro-o-anisic acid

HRID 330290Notes

Reaction equation

HRID 330290 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118574Methyl 5-chloro-2-methoxybenzoate

Product 1

HCID 769705-Chloro-o-anisic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 5-chloro-2-methoxybenzoate (23.1 g, 0.115 mol) in dioxane (300 mL) was added 2.5N NaOH (230 mL). The resulting mixture was stirred at room temperature for 4 hours, concentrated, diluted with H2O, and acidified with 2N HCl. 19.70 g (91%) of the desired product was collected by filtration as a white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O
  3. filtration19.70 g (91%) of the desired product was collected by filtration as a white solid

Sources & evidence

ORD record
ord-2eaaa2e16233494a8fc2f98e5807231f
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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