Ethanol → Ethyl γ-methyl-4-nitrobenzenebutanoate

HRID 638252Notes

Reaction equation

HRID 638252 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, 660 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% sodium bicarbonate, with water, dried over anhydrous sodium sulfate, filtered and evaporated to give 119 g (97%) of product. The product has bp 127°-128° C. (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% sodium bicarbonate, with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-39ef806542a8404386073e137e4d2d09
Source dataset
uspto-grants-1985_12
Patent number
US04560701

Reaction notes

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