Hydrochloric Acid → HCID 68984650, compound

HRID 2249622Notes

Reaction equation

HRID 2249622 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:10])([OH:3])=[O:2].[C:33](N1C=CN=C1)(N1C=CN=C1)=O.CO.Cl>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:21]([O:20][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:11]=1[C:9](=[O:10])[C:8]1[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[C:6]([CH2:5][CH2:4][C:1]([O:3][CH3:33])=[O:2])[CH:7]=1)[C:15]([OH:17])=[O:16])[CH:22]([CH3:23])[CH3:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 68988672HCID 68988672, compound

Product 1

HCID 68984650HCID 68984650, compoundYield 32.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2 ml of methylene chloride is dissolved 0.15 g of 4-[3-(2-carboxyethyl)-4-isobutoxybenzoyl]-3-isobutoxybenzoic acid, to which is added 0.12 g of 1,1′-carbonyldiimidazole. After stirring the mixture at ambient temperature for one hour, 15 μl of methanol is added, and the mixture thus obtained is stirred at the same temperature as above for one hour. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 2 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure to obtain 0.05 g of 3-isobutoxy-4-[4-isobutoxy-3-(3-methoxy-3-oxopropyl)benzoyl]benzoic acid as a white solid product.

Workup

  1. customthe mixture thus obtained
  2. stirringis stirred at the same temperature as above for one hour
  3. customthe organic layer is separated
  4. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-7a1146c22bb4497c822afd82d4a98b62
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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