Acetic Acid → HCID 13958739, compound

HRID 569261Notes

Reaction equation

HRID 569261 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[C:15]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].Cl.[CH3:24]NC.C=O.C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:16]([Cl:17])=[C:15]([C:18](=[O:22])[C:19](=[CH2:24])[CH2:20][CH3:21])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 13958738HCID 13958738, compound

Product 1

HCID 13958739HCID 13958739, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(2,3-dichloro-4-butyrylphenoxy)hexanoic acid (9.5 g, 0.026 mole), dimethylamine hydrochloride (15 g, 0.184 mole), paraformaldehyde (2.8 g, 0.09 equiv.) and acetic acid (1 ml) were united and stirred and heated on a steam bath for two hours. The reaction mixture was treated with N,N-dimethylformamide (30 ml) and stirring and heating continued for another hour. The reaction mixture was poured into ice water and the solid that separated was removed by filtration, washed with water and dried. The yield was 9.2 g after recrystallization from butyl chloride the 6-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]hexanoic acid melted at 106°-107° C.

Workup

  1. temperatureheated on a steam bath for two hours
  2. stirringstirring
  3. temperatureheating
  4. waitcontinued for another hour
  5. customthe solid that separated
  6. customwas removed by filtration
  7. washwashed with water
  8. customdried
  9. customThe yield was 9.2 g after recrystallization from butyl chloride the 6-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]hexanoic acid melted at 106°-107° C.

Sources & evidence

ORD record
ord-76ea6d4e26c048ea96a63438e177e8d1
Source dataset
uspto-grants-1988_03
Patent number
US04731473

Reaction notes

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