Hydrochloric Acid → 4-(2,3-Dichloro-4-butyrylphenoxy)butyric acid

HRID 255932Notes

Reaction equation

HRID 255932 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[O:14][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 140998561-(2,3-Dichloro-4-hydroxyphenyl)butan-1-one

Product 1

HCID 140998584-(2,3-Dichloro-4-butyrylphenoxy)butyric acidYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dichloro-4-butyrylphenol (69.9 g, 0.30 mole), potassium carbonate (75 g, 0.54 mole) and ethyl 4-bromobutyrate (87.8 g, 0.45 mole) in N,N-dimethylformamide (900 ml of sieve-dried material) were stirred and heated at 55°-60° C. for 16.5 hours. The mixture was then treated with 10 normal sodium hydroxide solution (120 ml) and water (600 ml) and stirring and heating at 100° C. maintained for 2 hours. The solution was cooled and poured into ice water (4 liters) containing concentrated hydrochloric acid (250 ml). The solid that separated was removed by filtration, washed with water and dried. The product (88 g) was recrystallized from butyl chloride (500 ml) to give 78.6 g of 4-(2,3-dichloro-4-butyrylphenoxy)butyric acid, m.p. 111°-113° C.

Workup

  1. temperatureheated at 55°-60° C. for 16.5 hours
  2. stirringstirring
  3. temperaturemaintained for 2 hours
  4. temperatureThe solution was cooled
  5. customThe solid that separated
  6. customwas removed by filtration
  7. washwashed with water
  8. customdried
  9. customThe product (88 g) was recrystallized from butyl chloride (500 ml)

Sources & evidence

ORD record
ord-ebdc4640ca0f4a65803e91fdac902575
Source dataset
uspto-grants-1987_10
Patent number
US04699926

Reaction notes

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