4-(Decyloxy)benzoic acid → 4-(5-Butoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl 4-decyloxybenzoate

HRID 1608902Notes

Reaction equation

HRID 1608902 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:21]([O:25][CH2:26][C:27]([F:44])([F:43])[C:28]([F:42])([F:41])[C:29]([F:40])([F:39])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[CH2:22][CH2:23][CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][C:35]2[CH:34]=[CH:33][C:32]([O:31][CH2:30][C:29]([F:39])([F:40])[C:28]([F:42])([F:41])[C:27]([F:43])([F:44])[CH2:26][O:25][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:37][CH:36]=2)=[O:17])=[CH:19][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 1385274-(Decyloxy)benzoic acidHCID 200827634-(5-Butoxy-2,2,3,3,4,4-hexafluoropentoxy)phenol

Product 1

HCID 200827514-(5-Butoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl 4-decyloxybenzoateYield 12.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.45 g (0.0016 moles) of 4-decyloxybenzoic acid and 0.58 g (0.0016 moles) of 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)phenol (prepared essentially as in Example 5) were dissolved in 25 ml of methylene chloride. N,N-dicyclohexylcarbodiimide (0.35 g, 0.0017 moles) was added to the reaction mixture, followed by 0.05 g of 4-(N,N-dimethylamino)pyridine. The resultant mixture was stirred at room temperature under nitrogen for 18 hours. The resulting urea precipitate was removed from the product solution by filtration, and the filtrate was concentrated on a rotary evaporator at reduced pressure. The crude product was purified by flash chromatography on silica gel (chloroform) to yield 0.12 g of 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl 4-decyloxybenzoate.

Workup

  1. customThe resulting urea precipitate was removed from the product solution by filtration
  2. concentrationthe filtrate was concentrated on a rotary evaporator at reduced pressure
  3. customThe crude product was purified by flash chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-b90baab25ce34140820eaa526c210927
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

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