Nitric Acid → Butyric Acid

HRID 258981Notes

Reaction equation

HRID 258981 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]12([C:15]3[CH:27]=[CH:26][C:18]([O:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2>C(O)(=O)C.C(Cl)Cl>[N+:1]([C:26]1[CH:27]=[C:15]([C:5]23[CH2:6][CH:7]4[CH2:8][CH:9]([CH2:10][CH:11]([CH2:13]4)[CH2:12]2)[CH2:14]3)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([O-:4])=[O:2].[C:23]([OH:25])(=[O:24])[CH2:22][CH2:21][CH3:20]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acid

Product 2

HCID 264Butyric AcidHCID 21425163HCID 21425163, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

120 ml of fuming nitric acid in 40 ml of glacial acetic acid are added dropwise to a solution of 31.4 g of 4-[4-(1-adamantyl)-phenoxy]-butyric acid in 100 ml of glacial acetic acid and 30 ml of methylene chloride at -5° C, whilst stirring in an aqueous atmosphere. After completion of the addition, the mixture is stirred for a further 15 minutes at -5° C and 30 minutes at -3° C. The reaction mixture is then poured onto 1 kg of ice and extracted with 3 times 200 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on 1 kg of silica gel, with ethyl acetate as the eluant, gives 4-[2-nitro-4-(1-adamantyl)-phenoxy]-butyric acid of melting point 182°-185° C (from methylene chloride/petroleum ether) and 4-[2,6;l -dinistro- 4-(1-adamantyl)-phenoxy]-butyric acid of melting point 170°-172° C (from ethanol-pentane).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture is stirred for a further 15 minutes at -5° C and 30 minutes at -3° C
  3. extractionextracted with 3 times 200 ml of methylene chloride
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac2c345b8d664d89a12780e6e8224669
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

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