Acetic Acid → HCID 86746454, compound

HRID 1645888Notes

Reaction equation

HRID 1645888 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[C:16]([CH3:22])=[CH:15][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10].[C:23](O)(=[O:25])[CH3:24]>[Fe]>[C:23]([NH:19][C:17]1[C:16]([CH3:22])=[CH:15][C:3]([O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([CH3:1])[CH:18]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86746451HCID 86746451, compound

Product 1

HCID 86746454HCID 86746454, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A mixture of 3.1 g (10 mmol) of the 5-(2,5-dimethyl-4-nitrophenoxy)-2,2-dimethylpentanoic acid, methyl ester (Example 1) and 2.0 g (3.5×10 mg-atom) of iron powder (40 mesh) in 35 mL of glacial acetic acid is stirred at reflux for 1.5 hours and poured into an ice-water mixture (300 mL). After scratching the oil crystallizes and the solid is collected on a filter, washed with water, and dried in vacuo at 40° C. The filtrate is extracted with dichloromethane. The extracts are washed with water, dried (magnesium sulfate), filtered, and evaporated leaving a medium brown oil which partially crystallizes. Recrystallization from 75 mL of isopropyl ether in the presence of charcoal affords 1.0 g of the title compound; mp 99°-100° C.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customcrystallizes
  3. customthe solid is collected on a filter
  4. washwashed with water
  5. customdried in vacuo at 40° C
  6. extractionThe filtrate is extracted with dichloromethane
  7. washThe extracts are washed with water
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated
  11. customleaving a medium brown oil which
  12. custompartially crystallizes
  13. customRecrystallization from 75 mL of isopropyl ether in the presence of charcoal

Sources & evidence

ORD record
ord-994459fd0db5478f8740903e9b489d21
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

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