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

HRID 255934Notes

Reaction equation

HRID 255934 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-cccb6ef04aba46429b3009859a33b55e
Source dataset
uspto-grants-1987_10
Patent number
US04699926

Reaction notes

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