Sodium Hydroxide → 4-(4-Chlorobutyloxy)benzoic acid

HRID 265892Notes

Reaction equation

HRID 265892 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=1.[OH-].[Na+].OS([O-])(=O)=O.[K+]>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 14575308Methyl 4-(4-chlorobutoxy)benzoate

Product 1

HCID 190341754-(4-Chlorobutyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 24-2 (3.0 g, 12.4 mmol), 1N NaOH (30 mL), and ethanol was heated at 60° C. for 1.0 hour. The cooled reaction mixture was acidified with 10% KHSO4 and then extracted with EtOAc. The EtOAc portion was washed with brine, dried (MgSO4) and concentrated to give 24-3 as a white solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. washThe EtOAc portion was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21803ed5b24647c39e159b4ca30aa559
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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