Triphenylphosphine → HCID 18429639, compound

HRID 2305055Notes

Reaction equation

HRID 2305055 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:13]=1O.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>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:15]=[C:14]([Cl:24])[C:13]=1[O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5563304-(Hydroxymethyl)benzaldehydeHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 18429639HCID 18429639, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3.40 g of p-(hydroxymethyl)benzaldehyde obtained in the same manner as described above, 7.2 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 6.56 g of triphenylphosphine, and 50 ml of tetrahydrofuran was slowly added dropwise 5.05 g of diisopropyl azodicarboxylate with stirring under ice cooling. 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 4.75 g (yield, 46%) of 4-((2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)methyl)benzaldehyde, m.p., 93.9° C.

Workup

  1. customobtained in the same manner
  2. stirringAfter stirring at room temperature for 12 hours
  3. concentrationthe reaction mixture was concentrated
  4. customto give a residue

Sources & evidence

ORD record
ord-58c279f28f05495b828ba3f903f194d7
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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