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

HRID 569258
Notes
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Reaction equation

HRID 569258 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-f8616e089a4a46f19d1baeaae8410855
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04731473

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes