Triphenylphosphine → 1-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)propan-2-one

HRID 2099930Notes

Reaction equation

HRID 2099930 reaction equation
C(OC(N=NC(OC(C)C)=O)=O)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:34][C:35]1[CH:45]=[C:44]([O:46][CH2:47][CH:48]=[C:49]([Cl:51])[Cl:50])[CH:43]=[C:42]([Cl:52])[C:36]=1[O:37][CH2:38][CH2:39][CH2:40][OH:41].O[C:54]1[CH:59]=[CH:58][C:57]([CH2:60][C:61](=[O:63])[CH3:62])=[CH:56][CH:55]=1>O1CCCC1>[Cl:34][C:35]1[CH:45]=[C:44]([O:46][CH2:47][CH:48]=[C:49]([Cl:51])[Cl:50])[CH:43]=[C:42]([Cl:52])[C:36]=1[O:37][CH2:38][CH2:39][CH2:40][O:41][C:54]1[CH:59]=[CH:58][C:57]([CH2:60][C:61](=[O:63])[CH3:62])=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70192744-HydroxyphenylacetoneHCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

Product 1

HCID 866054261-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

P4.1) At 0-2° C., 4.3 g of azodicarboxylic acid diisopropyl ester are added dropwise to 5.6 g of triphenylphosphine in 100 ml of tetrahydrofuran. After 30 minutes' stirring, a solution of 6.7 g of 3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propan-1-ol and 2.9 g of 1-(4-hydroxy-phenyl)-propan-2-one in 100 ml of tetrahydrofuran is added dropwise at 0-2° C. in the course of 45 minutes. After 2 hours at from 0 to 2° C. and 6 hours at room temperature, the reaction mixture is concentrated and the residue is purified over silica gel. 1-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propan-2-one is obtained. 1H-NMR (CDCl3) 300 MHz: 2.16 (s, 3H), 2.30 (m, 2H), 3.63 (s, 2H), 4.17 (t, 2H), 4.27 (t, 2H), 4.58 (d, 2H), 6.11 (t, 1H), 6.83 (s, 2H), 6.90 (d, 2H), 7.11 (d, 2H)

Workup

  1. waitAfter 2 hours at from 0 to 2° C. and 6 hours at room temperature
  2. concentrationthe reaction mixture is concentrated
  3. customthe residue is purified over silica gel

Sources & evidence

ORD record
ord-41fa9bc9309d481faa6878181dcd51f3
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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