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Oxalyl chloride → Ethyl 3-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isopentyloxyphenyl]propanoate

HRID 2249660
Notes
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Reaction equation

HRID 2249660 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][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)[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:33]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44]CC(C)C)[CH:39]=1)[CH:34]([CH3:36])[CH3:35]>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C)C=O>[OH:44][C:40]1[CH:39]=[C:38]([O:37][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:43]=[CH:42][C:41]=1[C:10]([C:9]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH:8]=1)=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 130875651,3-DiisobutoxybenzeneHCID 178165443-(3-Ethoxy-3-oxopropyl)-4-isopentyloxybenzoic acid

Product 1

HCID 17816495Ethyl 3-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isopentyloxyphenyl]propanoateYield 50.3%

Reagents, catalysts & solvents

3
HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In 9 ml of methylene chloride is dissolved 0.90 g of 3-(3-ethoxy-3-oxopropyl)-4-isopentyloxybenzoic acid. At ambient temperature, 0.31 ml of oxalyl chloride and 20 μl of N,N-dimethylformamide are successively added and the mixture thus obtained is stirred at ambient temperature for one hour. Then, at 5-10° C., 0.78 g of aluminum chloride and 0.78 g of 1,3-diisobutoxybenzene are successively added. The mixture thus obtained is stirred first at the same temperature as above for 30 minutes and then at ambient temperature for 30 minutes. Further, 0.39 g of aluminum chloride is added at ambient temperature and stirred at the same temperature as above for 30 minutes. The reaction mixture is added to a mixture of chloroform and ice water and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then 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 0.67 g of ethyl 3-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isopentyloxyphenyl]propanoate as a light yellow oily product.

Workup

  1. customthe mixture thus obtained
  2. customThe mixture thus obtained
  3. stirringis stirred first at the same temperature as above for 30 minutes
  4. waitat ambient temperature for 30 minutes
  5. stirringstirred at the same temperature as above for 30 minutes
  6. customthe organic layer is separated
  7. customThe organic layer thus obtained
  8. washis washed with water and saturated aqueous solution of sodium chloride successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue thus obtained
  12. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-87b807d768b14c0cbd799ff59f8865de
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314888B1

Reaction notes

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