Dicyclohexylcarbodiimide → 4-(4'-heptyl-1,1'-biphenyl-4-carbonyloxy)phenyl Vinyl Ketone

HRID 900024Notes

Reaction equation

HRID 900024 reaction equation
[CH:1]([C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4])=[CH2:2].[CH2:12]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH:1]([C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:31]([C:28]2[CH:27]=[CH:26][C:25]([C:22]3[CH:23]=[CH:24][C:19]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:20][CH:21]=3)=[CH:30][CH:29]=2)=[O:32])=[CH:9][CH:10]=1)=[O:4])=[CH2:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 30863554-(4-Heptylphenyl)benzoic AcidHCID 160369274-Acryloylphenol

Product 1

HCID 596958064-(4'-heptyl-1,1'-biphenyl-4-carbonyloxy)phenyl Vinyl KetoneYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxyphenyl vinyl ketone (c) (1 g), 4′-heptyl-1,1′-biphenyl-4-carboxylic acid (1.8 g), DCC (1.9 g) DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The solvent was evaporated away, and the residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.5 g of colorless crystals, compound (1-13-8). The NMR and MS spectra of the compound well support the structure thereof.

Workup

  1. customThe white solid precipitated
  2. filtrationwas filtrated out
  3. customthe solvent was evaporated away from the filtrate
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with aqueous 2 M NaOH solution
  6. customThe solvent was evaporated away
  7. customthe residue was purified through column chromatography (eluent: toluene)
  8. customthrough recrystallization (ethanol)

Sources & evidence

ORD record
ord-6e965ca5f88545199d4b51b30425a24f
Source dataset
uspto-grants-2008_04
Patent number
US07357964B2

Reaction notes

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