Dimethylformamide → 3,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-2-propenyloxy)butyloxy)benzene

HRID 369657Notes

Reaction equation

HRID 369657 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:22])[CH:6]=[C:7]([CH2:20][CH3:21])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH3:2].[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:20]([C:7]1[CH:6]=[C:5]([O:22][CH2:26][CH:25]=[C:24]([Cl:28])[Cl:23])[CH:4]=[C:3]([CH2:1][CH3:2])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 232823733,5-Diethyl-4-(4-(3,3-dichloro-2-propenyloxy)butyloxy)phenol

Product 1

HCID 232823693,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-2-propenyloxy)butyloxy)benzeneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 0.35 g of 3,5-diethyl-4-(4-(3,3-dichloro-2-propenyloxy)butyloxy)phenol, 0.16 g of 1,1,3-trichloro-1-propene, 0.15 g of potassium carbonate and 10 ml of N,N-dimethylformamide. After stirring at room temperature for 24 hours, the reaction mixture was poured into water and extracted twice with 50 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated. The residue was subjected to silica gel chromatography, which afforded 0.33 g of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-2-propenyloxy)butyloxy)benzene (yield, 72%), nD24.4 1.5311.

Workup

  1. extractionextracted twice with 50 ml of diethyl ether
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1991e42ff5074b4fbbab4d50391b7b85
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

Loading…