Potassium Iodide → 4-(4-Hydroxybutoxy)benzoic acid

HRID 355597

Reaction equation

HRID 355597 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8]Cl)(=O)C.[OH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 233991-Butanol, 4-chloro-, 1-acetate

Product 1

HCID 152185964-(4-Hydroxybutoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chlorobutyl acetate (276.6 g; 1.8 mol) is added to a solution of ethyl 4-hydroxybenzoate (249 g; 1.5 mol), potassium iodide (3 g) and potassium carbonate (248 g; 1.8 mol) in dimethylformamide (2 l), and the mixture is stirred at 90° C. for 11 hours. The reaction mixture is transferred into 5 l of ice water, and the resultant precipitate is filtered off with suction and washed with 4 to 5 l of ice water. The crude product is dissolved in 3 l of ethanol, potassium hydroxide (400 g) is added, and the mixture is refluxed for 3 hours. The reaction mixture is transferred into 6 l of ice water, and acidified by means of concentrated hydrochloric acid, and the precipitate is filtered off, washed with water until neutral and then dried.

Workup

  1. filtrationthe resultant precipitate is filtered off with suction
  2. washwashed with 4 to 5 l of ice water
  3. dissolutionThe crude product is dissolved in 3 l of ethanol
  4. additionpotassium hydroxide (400 g) is added
  5. temperaturethe mixture is refluxed for 3 hours
  6. filtrationthe precipitate is filtered off
  7. washwashed with water until neutral and
  8. customthen dried

Sources & evidence

ORD record
ord-003226eb613840aabf6b207b6d5d65a7
Source dataset
uspto-grants-1998_11
Patent number
US05833880

Linked notes

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