Acrylic Acid → HCID 18979457, compound

HRID 2392589Notes

Reaction equation

HRID 2392589 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17].[C:40](O)(=[O:43])[CH:41]=[CH2:42]>CN(C)C1C=CN=CC=1.ClCCl>[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:43])[CH:41]=[CH2:42])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 18979506HCID 18979506, compound

Product 1

HCID 18979457HCID 18979457, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.9 g of N,N'-dicyclohexylcarbodiimide were added within 5 minutes while stirring to a solution of 3.8 g of 4-formyl-4'-(8-hydroxyoctyloxy)biphenyl, 0.9 g of acrylic acid and 0.05 g of 4-(dimethylamino)pyridine in 25 ml of dichloromethane. The reaction mixture was stirred overnight, filtered and then concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which were pure according to thin-layer chromatography gave 2.5 g of 4-formyl-4'-(8-acryloyloxyoctyloxy)biphenyl.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which

Sources & evidence

ORD record
ord-e8dc56b416c84bff844df391b51b7311
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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