Methanol → HCID 13134408, compound

HRID 1443153Notes

Reaction equation

HRID 1443153 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])C(OC)=O.Cl(O)(=O)(=O)=O.C(OCC)(=O)C.CO>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 24247Perchloric AcidHCID 13134407Dimethyl (2,6-dinitrophenyl)propanedioate

Product 1

HCID 13134408HCID 13134408, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

10.08 g (33.8 mmol) of dimethyl-2-(2,6-dinitrophenyl)-malonate is mixed in 54 ml of glacial acetic acid with 2.7 ml of perchloric acid and refluxed at 125° C. In this case, the ethyl acetate that is produced is distilled off. After 90 minutes, the reaction is brought to a halt, since starting material is no longer present according to TLC. The reaction mixture is poured into ice water and extracted three times with ethyl acetate. The combined organic extracts are shaken with 5% sodium bicarbonate solution, with water and with brine. After the organic phase is dried, the desiccant is filtered off and the solvent is spun off, a residue remains that is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 4.69 g of the (2,6-dinitrophenyl)-acetic acid, which then is esterified with methanol (16 ml) and concentrated sulfuric acid (0.4 ml), is isolated. To this end, the acid and the reagents are refluxed for seven hours. The methanol is spun off, and the residue is worked up in the usual way. After chromatography on silica gel (mobile solvent:ethyl acetate/hexane), 4.43 g (89%) of the desired ester is obtained.

Workup

  1. distillationis distilled off
  2. additionThe reaction mixture is poured into ice water
  3. extractionextracted three times with ethyl acetate
  4. customAfter the organic phase is dried
  5. filtrationthe desiccant is filtered off
  6. customthat is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)
  7. customis isolated
  8. temperatureTo this end, the acid and the reagents are refluxed for seven hours

Sources & evidence

ORD record
ord-7182f91c294641c080cfa39cc40d30dd
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

Loading…