Ethanol → Ethyl γ-methyl-4-nitrobenzenebutanoate

HRID 1085197Notes

Reaction equation

HRID 1085197 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17](O)[CH3:18]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:16])[CH2:11][CH2:12][C:13]([O:15][CH2:17][CH3:18])=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 12561712HCID 12561712, compound

Product 1

HCID 12561711Ethyl γ-methyl-4-nitrobenzenebutanoateYield 97%

Procedure

A mixture of 110 g of 4-(4-nitrophenyl)valeric acid, 600 ml of absolute ethanol and 10 ml of concentrated sulfuric was heated under reflux overnight. The ethanol was evaporated in vacuo and the residue was partitioned between ether and water. The ether extract was washed with 5% of sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, filtered and evaporated to give 119 g (97%) of product, bp 127°-128° (1.5 mm).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe ethanol was evaporated in vacuo
  4. customthe residue was partitioned between ether and water
  5. extractionThe ether extract
  6. washwas washed with 5% of sodium bicarbonate solution and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6caa2df8b0e04af688f8ade6ad6b7a50
Source dataset
uspto-grants-1991_04
Patent number
US05008285

Reaction notes

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