Acetic Acid → 5-[2,3-Dichloro-4-(2-methylidenebutanoyl)phenoxy]pentanoic acid

HRID 569116Notes

Reaction equation

HRID 569116 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].Cl.[CH3:23]NC.C=O.C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:15]([Cl:16])=[C:14]([C:17](=[O:21])[C:18](=[CH2:23])[CH2:19][CH3:20])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 139587375-(2,3-Dichloro-4-butyrylphenoxy)valeric acid

Product 1

HCID 139587365-[2,3-Dichloro-4-(2-methylidenebutanoyl)phenoxy]pentanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2,3-Dichloro-4-butyrylphenoxy)valeric acid (9.8 g, 0.029 mole), dimethylamine hydrochloride (15 g, 0.184 mole), paraformaldehyde (2.8 g, 0.09 equivalent) and acetic acid (1 ml) were united and stirred and heated on a steam bath for 3 hours. N,N-dimethylformamide (30 ml) was added and stirring and heating continued for another two hours. The reaction mixture was then poured into ice water and the solid that separated was removed by filtration, washed with water and dried. After recrystallization from butyl chloride the 5-[2,3-dichloro-(2-methylenebutyryl)phenoxy]valeric acid (5.4 g) melted at 107°-109° C.

Workup

  1. temperatureheated on a steam bath for 3 hours
  2. stirringstirring
  3. temperatureheating
  4. customthe solid that separated
  5. customwas removed by filtration
  6. washwashed with water
  7. customdried
  8. customAfter recrystallization from butyl chloride the 5-[2,3-dichloro-(2-methylenebutyryl)phenoxy]valeric acid (5.4 g) melted at 107°-109° C.

Sources & evidence

ORD record
ord-ee4b96b36eb44e32bd792b6e7fc0fb1f
Source dataset
uspto-grants-1988_03
Patent number
US04731381

Reaction notes

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