4-Hydroxybenzaldehyde → HCID 18979539, compound

HRID 2392584Notes

Reaction equation

HRID 2392584 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.O[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:47]=[CH:46][C:42]([C:43]([OH:45])=[O:44])=[CH:41][CH:40]=1)(=[O:28])[CH:26]=[CH2:27]>CN(C)C1C=CN=CC=1.ClCCl>[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([C:43]([O:45][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)=[O:44])=[CH:46][CH:47]=1)(=[O:28])[CH:26]=[CH2:27]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10868DicyclohexylcarbodiimideHCID 541130724-{[8-(Acryloyloxy)octyl]oxy}benzoic acid

Product 1

HCID 18979539HCID 18979539, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3.9 g of N,N'-dicyclohexylcarbodiimide were added at 0° C. within 15 minutes while stirring to a solution of 1.9 g of 4-hydroxybenzaldehyde, 5.0 g of 4-[8-acryloyloxyoctyloxy]benzoic acid and 0.1 g of 4-(dimethylamino)pyridine in 100 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight, filtered and the filtrate was concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from ethyl acetate of the fractions which were pure according to thin-layer chromatography gave 5.5 g of 4-(4-[8-acryloyloxyoctyloxy]phenylcarbonyloxy)benzaldehyde; m.p. 73° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customChromatographic purification of the residue on silica gel
  4. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from ethyl acetate of the fractions which

Sources & evidence

ORD record
ord-70d655116db5408b80f61c1ba14ec0d5
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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