4-Hydroxybenzaldehyde → HCID 11745419, compound

HRID 375015Notes

Reaction equation

HRID 375015 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.[C:25](O)(=[O:29])/[CH:26]=[CH:27]/[CH3:28]>CN(C)C1C=CN=CC=1.ClCCl>[C:25]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1)(=[O:29])/[CH:26]=[CH:27]/[CH3:28]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10868DicyclohexylcarbodiimideHCID 637090Crotonic Acid

Product 1

HCID 11745419HCID 11745419, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

17.8 g of N,N'-dicyclohexylcarbodiimide were added while stirring within 5 minutes to a solution of 7.0 g of 4-hydroxybenzaldehyde, 7.4 g of (E)-but-2-enoic acid and 0.1 g of 4-(dimethylamino)pyridine in 50 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered. The filtrate was washed with saturated sodium bicarbonate solution and with water and concentrated. Chomatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 3:7) and two-fold recrystallization of the fractions which were pure according to thin-layer chromatography gave 12.2 g of 4-[(E)-but-2-enoyloxy]benzaldehyde.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with saturated sodium bicarbonate solution and with water
  3. concentrationconcentrated
  4. customChomatographic purification of the residue on silica gel
  5. customwith hexane/ethyl acetate (vol. 3:7) and two-fold recrystallization of the fractions which

Sources & evidence

ORD record
ord-098e69c699b84540a7945c2cc7b85951
Source dataset
uspto-grants-1996_01
Patent number
US05484551

Reaction notes

Loading…