Acetic Acid → 1-[2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]cyclobutane-1-carboxylic acid

HRID 569262Notes

Reaction equation

HRID 569262 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][C:5]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][CH2:6]1.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][C:5]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 201486981-(2,3-Dichloro-4-butyrylphenoxy)cyclobutane-1-carboxylic acid

Product 1

HCID 139587401-[2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]cyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2,3-dichloro-4-butyrylphenoxy)cyclobutane-1-carboxylic acid (4 g, 0.012 mole), dimethylamine hydrochloride (5.5 g, 0.067 mole), paraformaldehyde (1.2 g, 0.04 equiv.) and acetic acid (0.3 ml) were stirred and heated on a steam bath for 2.25 hours. N,N-dimethylformamide (30 ml) was added and stirring and heating was continued for another 2 hours. The mixture was poured into ice water and extracted with ether. The ether layer was washed with water and then with brine and finally dried over MgSO4. The solution was treated with p-xylene and the solvents were removed in vacuo. The resulting residue was recrystallized from hexane to give 1-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]cyclobutane-1-carboxylic acid, m.p. 120° C.

Workup

  1. temperatureheated on a steam bath for 2.25 hours
  2. stirringstirring
  3. temperatureheating
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialwith brine and finally dried over MgSO4
  7. additionThe solution was treated with p-xylene
  8. customthe solvents were removed in vacuo
  9. customThe resulting residue was recrystallized from hexane

Sources & evidence

ORD record
ord-4a66fb8ce66d433fb7bb5a327e5c3668
Source dataset
uspto-grants-1988_03
Patent number
US04731473

Reaction notes

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