Triphenylphosphine → HCID 54294615, compound

HRID 1280218Notes

Reaction equation

HRID 1280218 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].[Cl:16][C:17]([Cl:31])=[CH:18][CH2:19][O:20][N:21]=[CH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Cl:16][C:17]([Cl:31])=[CH:18][CH2:19][O:20][N:21]=[CH:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][O:15][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])=[CH:5][C:4]=2[Cl:14])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 54435005HCID 54435005, compound

Product 1

HCID 54294615HCID 54294615, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.35 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.32 g of 4-(hydroxymethyl)benzaldehyde O-(3,3-dichloro-2-propenyl)oxime, 0.32 g of triphenylphosphine, and 10 ml of dichloromethane was slowly added dropwise 0.25 g of diisopropyl azodicarboxylate. After stirring at room temperature for 12 hours, the reaction mixture was concentrated to give a residue. This residue was subjected to silica gel chromatography, which afforded 0.43 g (yield, 67%) of 4-((2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)methyl)benzaldehyde O-(3,3-dichloro-2-propenyl)oxime, m.p., 76.2° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a residue

Sources & evidence

ORD record
ord-980f7261745f4b27b885dbc5e2c271b6
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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