Ethylparaben → 4-(4-Hydroxybutoxy)benzoic acid

HRID 1019328

Reaction equation

HRID 1019328 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.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C=O)C>[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 3

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

Product 1

HCID 152185964-(4-Hydroxybutoxy)benzoic acidYield 89.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

276.6 g of 4-chlorobutyl acetate (1.8 mol) were added to a solution of 249 g of ethyl 4-hydroxybenzoate (1.5 mol), 3 g of potassium iodide (0.018 mol) and 248 g of potassium carbonate (1.8 mol) in 21 of DMF, and the mixture was stirred at 90° C. for 11 hours. The reaction mixture was poured into 5 l of ice-water, and the precipitate was filtered off with suction and washed with 41 of ice-water. The crude product was dissolved in 3 l of ethanol, potassium hydroxide (400 g) was added, and the mixture was refluxed for 3 hours. The reaction mixture was poured into 6 l of ice-water and acidified using concentrated hydrochloric acid, and the precipitate was filtered off. The precipitate was washed with water until neutral and subsequently dried, giving 282.1 g of 4-(4′-hydroxybutoxy)benzoic acid (yield 89%).

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed with 41 of ice-water
  3. dissolutionThe crude product was dissolved in 3 l of ethanol
  4. additionpotassium hydroxide (400 g) was added
  5. temperaturethe mixture was refluxed for 3 hours
  6. additionThe reaction mixture was poured into 6 l of ice-water
  7. filtrationthe precipitate was filtered off
  8. washThe precipitate was washed with water until neutral and
  9. customsubsequently dried

Sources & evidence

ORD record
ord-997e80863f7e40ffab1855ebc2c7920c
Source dataset
uspto-grants-2002_11
Patent number
US06486338B1

Linked notes

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