Cycloheptanone → HCID 54547153, compound

HRID 1781601Notes

Reaction equation

HRID 1781601 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[C:11]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>P(=O)(O)(O)O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:11]2=[O:18])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 10400CycloheptanoneHCID 660424-Cyanobenzaldehyde

Product 1

HCID 54547153HCID 54547153, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20.0 g of 4-cyanobenzaldehyde, 30.5 g of cycloheptanone, and 200 mL of 85% phosphoric acid is heated for 1.5 h at 100° C. The mixture is cooled to room temperature, and filtered. The filtrate is poured into water (800 mL), and the precipitate is filtered, washed with water, and dried. The solid is purified by flash chromatography eluting with a mixture of ether:hexane, 1:2 to afford (4-cyanophenylmethylene)cycloheptanone.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate is poured into water (800 mL)
  4. filtrationthe precipitate is filtered
  5. washwashed with water
  6. customdried
  7. customThe solid is purified by flash chromatography
  8. washeluting with a mixture of ether

Sources & evidence

ORD record
ord-1a15931d453046db9c51382d25968c1b
Source dataset
uspto-grants-1997_05
Patent number
US05633381

Reaction notes

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