4-Nitrobenzaldehyde → HCID 11536760, compound

HRID 2251725Notes

Reaction equation

HRID 2251725 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].C1(C)C=CC=CC=1>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[O:1][CH2:2][C:3]3[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=3[CH2:9][O:10]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 114692971,2,4-Benzenetrimethanol

Product 1

HCID 11536760HCID 11536760, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 71586775BentoniteCatalystHCID 1140TolueneSolvent

Procedure

10 g of (3,4-bis-hydroxymethylphenyl)methanol (59.4 mmol) (prepared according to Nakazaki, M.; Yamamoto, K. And Miura, Y.; J. Org. Chem., 43(6), (1978), 1041-1044), 100 ml of toluene, 8.98 g of 4-nitrobenzaldehyde (59.4 mmol) and 0.6 g of Montmorillonite KSF (10 mg/mmol) are introduced into a flask equipped with a Dean-Stark. The mixture is heated under reflux for 2 hours 30 minutes. The montmorillonite is filtered off and the reaction medium is allowed to return to room temperature, with stirring. The reaction product crystallizes. After filtration and drying under vacuum at 50° C., 11.2 g of [7-(4-nitrophenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl]methanol are obtained.

Workup

  1. customequipped with a Dean-Stark
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 2 hours 30 minutes
  4. filtrationThe montmorillonite is filtered off
  5. customto return to room temperature
  6. customThe reaction product crystallizes
  7. filtrationAfter filtration
  8. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-4a78cfa256664198abd1b080834c180d
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

Loading…