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

HRID 1280243Notes

Reaction equation

HRID 1280243 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:25])[CH:6]=[C:7]([CH2:23][CH3:24])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:2].[Cl:26][C:27]([Cl:31])=[CH:28][CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:23]([C:7]1[CH:6]=[C:5]([O:25][CH2:29][CH:28]=[C:27]([Cl:31])[Cl:26])[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]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 184295323,5-Diethyl-4-(4-(2,2-diethoxyethoxy)butyloxy)phenol

Product 1

HCID 184299913,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzeneYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 19.9 g of 3,5-diethyl-4-(4-(2,2-diethoxyethoxy)butyloxy)phenol, 9.20 g of 1,1,3-trichloro-1-propene, 9.15 g of potassium carbonate, and 200 ml of N,N-dimethylformamide were placed in a reaction vessel. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium, and concentrated to give a residue. This residue was subjected to silica gel chromatography, which afforded 25.4 g (yield, 91%) of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene, nD26.0 1.4991.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium
  4. concentrationconcentrated
  5. customto give a residue

Sources & evidence

ORD record
ord-2b3b6abd53b548bb80c0563a24aa0c89
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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