Hydrochloric Acid → 5-(2,3-Dichloro-4-butyrylphenoxy)valeric acid

HRID 569260Notes

Reaction equation

HRID 569260 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][CH2:25][C:26]([O:28]CC)=[O:27].[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][CH2:25][C:26]([OH:28])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 84580Ethyl 5-bromovalerateHCID 140998561-(2,3-Dichloro-4-hydroxyphenyl)butan-1-one

Product 1

HCID 139587375-(2,3-Dichloro-4-butyrylphenoxy)valeric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,3-dichloro-4-butyrylphenol (7 g, 0.03 mole), potassium carbonate (7.5 g, 0.054 mole) and ethyl 5-bromovalerate (9.5 g, 0.045 mole) in N,N-dimethylformamide (60 ml) were stirred and heated at 60° C. for 3 hours. The mixture was treated with 10 normal sodium hydroxide (12 ml) and water (50 ml), then stirred and heated on a steam bath for 2.5 hours. The solution was poured into ice water containing hydrochloric acid. The solid that separated was removed by filtration, washed with water and dried. The product (9.8 g) was recrystallized from butyl chloride to give 5-(2,3-dichloro-4-butyrylphenoxy)valeric acid, m.p. 102°-103° C.

Workup

  1. stirringstirred
  2. temperatureheated on a steam bath for 2.5 hours
  3. customThe solid that separated
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried
  7. customThe product (9.8 g) was recrystallized from butyl chloride

Sources & evidence

ORD record
ord-c8be41e1965d4e729271346f514fcdb7
Source dataset
uspto-grants-1988_03
Patent number
US04731473

Reaction notes

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