Methyl Ethyl Ketone → HCID 637212, compound

HRID 1741947Notes

Reaction equation

HRID 1741947 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C1(S(O[C@H:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH3:27])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CC(CC)=O>O>[N+:13]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[O:1][C@@H:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH3:27])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 87895Benzoic acid, 4-hydroxy-3-nitro-, ethyl esterHCID 53696974HCID 53696974, compound

Product 1

HCID 637212HCID 637212, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4 g of ethyl 4-hydroxy-3-nitrobenzoate, 5.4 g of (S)-2-octyl benzenesulphonate 6.9 g of potassium carbonate and 110 ml of ethyl methyl ketone was heated to reflux overnight. Subsequently, the cooled reaction mixture was poured into water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with 500 ml of water, dried over magnesium sulphate, filtered and concentrated. Chromatography of the residue on silica gel with dichloromethane gave 5.6 g of ethyl 3-nitro-4-[(R)-2-octyloxy)benzoate as of a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customSubsequently, the cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fa8dbd78b4bb4111acd041d8a43c9723
Source dataset
uspto-grants-1994_08
Patent number
US05335303

Reaction notes

Loading…