Methanol → HCID 23282353, compound

HRID 369672Notes

Reaction equation

HRID 369672 reaction equation
[CH2:1]([C:3]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([CH2:24][CH3:25])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=[O:13])[CH3:2].[Cl-].[NH4+].[C:28](=[O:31])([O-])O.[Na+].[CH3:33]O>>[CH2:24]([C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:17]=[C:3]([CH2:1][CH3:2])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([O:31][CH3:28])[O:13][CH3:33])[CH3:25]

Participants

5

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 54234953HCID 54234953, compound

Product 1

HCID 23282353HCID 23282353, compoundYield 71%

Procedure

First, 0.39 g of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde was dissolved in 10 ml of anhydrous methanol, to which 5 mg of ammonium chloride was added, and the mixture was heated under reflux for 3 hours After left alone for cooling, the reaction mixture was mixed with 10 ml of saturated aqueous sodium hydrogencarbonate solution. The methanol was distilled out, and the residue was extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.31 g of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-dimethoxyethoxy)butyloxy)benzene (yield, 71%), nD24.0 1.5068.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. waitAfter left alone
  5. temperaturefor cooling
  6. distillationThe methanol was distilled out
  7. extractionthe residue was extracted twice with diethyl ether
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customto give a crude product

Sources & evidence

ORD record
ord-dc50677cc49b4df6b16d5ea8a692ee00
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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