Phthalaldehyde → HCID 71434730, compound

HRID 1708909Notes

Reaction equation

HRID 1708909 reaction equation
C1(P(=[CH:20][C:21]#[N:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:23]1[CH:24]=[CH:25][C:26]([CH:31]=O)=[C:27]([CH:29]=[O:30])[CH:28]=1>ClCCl>[CH:29]([C:27]1[CH:28]=[CH:23][CH:24]=[CH:25][C:26]=1[CH:31]=[CH:20][C:21]#[N:22])=[O:30]

Participants

4

Reactant 2

HCID 4807PhthalaldehydeHCID 85524(Triphenylphosphoranylidene)acetonitrile

Product 1

HCID 71434730HCID 71434730, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphoranylidene acetonitrile (13 g) in dry dichloromethane (20 ml) was added to a solution of ortho phthalaldehyde (5.4 g) in dry dichloromethane (20 ml), at 0°. The solution was stirred at room temperature for 1 h, then the solvent evaporated and the oil taken up with diethyl ether. The solid was filtered, washed with ether and the solution evaporated to dryness to give a yellow oil, which was eluted on a silica gel column (gradient petrol ether/diethyl ether, 1:1) to give the (E)-isomer of the title compound (0.9 g) and the (Z)-isomer of the title compound (2 g) (eluted first) as white solids which were recrystallized from petrol ether/diethyl ether (9:1).

Workup

  1. customthe solvent evaporated
  2. filtrationThe solid was filtered
  3. washwashed with ether
  4. customthe solution evaporated to dryness
  5. customto give a yellow oil, which
  6. washwas eluted on a silica gel column (gradient petrol ether/diethyl ether, 1:1)

Sources & evidence

ORD record
ord-7c4c4f20088943518d4c15fb43ed5d8c
Source dataset
uspto-grants-1990_08
Patent number
US04946851

Reaction notes

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