Dimethylformamide → HCID 17816502, compound

HRID 2249633Notes

Reaction equation

HRID 2249633 reaction equation
[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:10]([OH:12])=O)[CH2:2][CH:3]([CH3:5])[CH3:4].CN(C)C=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:31]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44]([O:46][CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])=[O:45])[CH2:32][CH:33]([CH3:35])[CH3:34]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:10]([C:40]1[CH:41]=[CH:42][C:37]([O:36][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[C:38]([CH2:43][C:44]([O:46][CH2:47][CH2:48][CH:49]([CH3:50])[CH3:51])=[O:45])[CH:39]=1)=[O:12])[CH2:2][CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6451240Aluminum(III) ChlorideHCID 17816448HCID 17816448, compoundHCID 17816487HCID 17816487, compound

Product 1

HCID 17816502HCID 17816502, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In 8 ml of methylene chloride is dissolved 0.80 g of 3,4-diisopentyloxybenzoic acid. Then, 20 μl of N,N-dimethylformamide is added, and the mixture thus obtained is stirred at ambient temperature for one hour. To the mixture thus obtained are successively added 1.10 g of aluminum chloride and 0.95 g of isopentyl 2-(2-isopentyloxyphenyl)acetate at 5-10° C., and the mixture thus obtained is stirred at 5-10° C. for 10 minutes. The reaction mixture is added to a mixture of chloroform and ice water, and the organic layer is separated. After washing the organic layer with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to obtain 1.20 g of isopentyl 2-[5-(3,4-diisopentyloxybenzoyl)-2-isopentyloxyphenyl]-acetate as a yellow oily product.

Workup

  1. customthe mixture thus obtained
  2. customTo the mixture thus obtained
  3. customat 5-10° C.
  4. customthe mixture thus obtained
  5. stirringis stirred at 5-10° C. for 10 minutes
  6. customthe organic layer is separated
  7. washAfter washing the organic layer with water and saturated aqueous solution of sodium chloride successively
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe residue thus obtained
  11. customis purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-44d9de3cf8c844979a84a13546446f09
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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