Hydrochloric Acid → HCID 53790038, compound

HRID 579998Notes

Reaction equation

HRID 579998 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8].C(N)CCC.[N+:21]([CH2:24][CH2:25]C)([O-:23])=[O:22].Cl>C(O)(=O)C.O.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:13]=[C:12]([CH:14]=[C:24]([N+:21]([O-:23])=[O:22])[CH3:25])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79031-NitropropaneHCID 8007ButylamineHCID 686916(4-formyl-2-methoxyphenoxy)acetic acid

Product 1

HCID 53790038HCID 53790038, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

(2-Methoxy-4-formylphenoxy)acetic acid (10.5 g, 0.05 mole), butylamine (14.6 g, 0.2 mole) and benzene were united and refluxed in a flask equipped with a Dean-Stark water separator. The mixture was refluxed for 4 hours and then the benzene removed by distillation at reduced pressure. The residue consisted of 2-methoxy-4-(butyliminomethylene)-phenoxy)acetic acid which was treated with nitro-propane (17.8 g, 0.2 mole) and acetic acid (50 ml) and heated to boiling. After standing for 30 minutes the mixture was poured into crushed ice and acidified with hydrochloric acid. The solid that separated was removed by filtration, washed with water, dried and recrystallized first from a mixture of water and isopropyl alcohol (3:1) and then from a mixture of benzene and hexane (4:3) to give product melting at 116°-117° C.

Workup

  1. temperaturerefluxed in a flask
  2. temperatureThe mixture was refluxed for 4 hours
  3. customthe benzene removed by distillation at reduced pressure
  4. temperatureheated to boiling
  5. additionthe mixture was poured
  6. custominto crushed ice
  7. customThe solid that separated
  8. customwas removed by filtration
  9. washwashed with water
  10. customdried
  11. customrecrystallized first from a mixture of water and isopropyl alcohol (3:1)
  12. additionfrom a mixture of benzene and hexane (4:3)

Sources & evidence

ORD record
ord-cfe933bd1e2e43ee94ba1f196bf48b24
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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