Hydrochloric Acid → Ethyl-12-(m-iodophenyl)-dodecanoate

HRID 2226289Notes

Reaction equation

HRID 2226289 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](N)[CH:18]=1)[CH3:3].N([O-])=O.[Na+].[I:29]I>CCOCC.C(O)(=O)C>[CH2:2]([O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([I:29])[CH:18]=1)[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 14584161Ethyl-12-(m-aminophenyl)-dodecanoateHCID 23668193Sodium Nitrite

Product 1

HCID 14584162Ethyl-12-(m-iodophenyl)-dodecanoateYield 174.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Glacial acetic acid (4 ml) and concentrated HCl (2.5 ml) were added to a 50 ml Erlenmeyer flask containing ethyl-12-(m-aminophenyl)-dodecanoate (3.92 g, 12.28 mmol). The mixture was cooled in a NaCl/ice bath. A cold aqueous solution of NaNO2 (4 ml, 3.1M) was added to the mixture. The reaction was stirred for 40 minutes before a cold aqueous solution of KI/I2 (2.31/1.78 g, 7 ml) was added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Ether was added to the reaction mixture. The ether layer was separated and extracted with H2O, 10% Na2S2O3, H2O, sat. NaHCO3, and brine. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a reddish oil. The crude product was purified by column chromatography (120 g silica gel, hexanes:ethyl acetate 20:1) to yield a clear oil, compound 6, ethyl-12-(m-iodophenyl)-dodecanoate (5.28 g, 56.8% yield).

Workup

  1. temperatureThe mixture was cooled in a NaCl/ice bath
  2. additionwas added
  3. customThe ether layer was separated
  4. extractionextracted with H2O, 10% Na2S2O3, H2O, sat. NaHCO3, and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a reddish oil
  8. customThe crude product was purified by column chromatography (120 g silica gel, hexanes:ethyl acetate 20:1)

Sources & evidence

ORD record
ord-9a419fb1f6604ca98f655efcb82714aa
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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