Phenol → HCID 54265828, compound

HRID 363066Notes

Reaction equation

HRID 363066 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].[C:16]1(O)C=CC=C[CH:17]=1.[Cl:23][C:24]1[CH:25]=[C:26](O)[CH:27]=[CH:28][C:29]=1OCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[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[O:15][CH2:16][CH2:17][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[CH:25]=1

Participants

7

Reactant 5

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 13668154HCID 13668154, compound

Product 1

HCID 54265828HCID 54265828, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, phenol, 0.16 g of 3-chlorophenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After siring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.36 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-chlorophenyl)ethoxy)benzene (81% yield), nD26.0 1.5897.

Workup

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

Sources & evidence

ORD record
ord-9d0105ea80e14a5ab944d1823039aaae
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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