Methyl 3-chloro-4-isopropoxybenzoate → 3-Chloro-4-(propan-2-yloxy)benzoic acid

HRID 2192463Notes

Reaction equation

HRID 2192463 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([O:7]C)=[O:6]>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoate

Product 1

HCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (D2; 100 g) was taken up in a mixture of methanol (555 ml) and 2N NaOH solution (555 ml). An insoluble white suspension was observed but with time complete solubility was observed. The reaction was stirred at room temperature overnight and the excess methanol was removed by evaporation until water was coming over. The basic solution was acidified to pH 1-2 and a white solid was filtered off which was washed with water (500 ml) and dried in vacuo overnight to give the title compound (82 g).

Workup

  1. customthe excess methanol was removed by evaporation until water
  2. filtrationa white solid was filtered off which
  3. washwas washed with water (500 ml)
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-8d8ce160056647a1b47f5ddf3df19a1f
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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