Sodium Hydroxide → 4-(3-chloropropoxy)benzoic Acid

HRID 251451Notes

Reaction equation

HRID 251451 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 46108434-(3-chloropropoxy)benzoic AcidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-(3-chloropropoxy)benzoate ax13 (3 g, 13 mmol, 1 eq) in ethanol (30 ml) is added 2.5 M aqueous sodium hydroxide (10 ml, 25 mmol, 2 eq). The mixture is refluxed for 1 hour, concentrated under vacuum, acidified with 2 M aqueous hydrochloric acid to pH 1 and extracted with ethyl acetate (3×50 ml). The combined organic layers are evaporated to give 2.75 g of 4-(3-chloropropoxy)benzoic acid ax51.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. concentrationconcentrated under vacuum
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe combined organic layers are evaporated

Sources & evidence

ORD record
ord-252fcb5925174eb3b802e5964b3e2c15
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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