Hydroquinone → HCID 68134387, compound

HRID 1973770Notes

Reaction equation

HRID 1973770 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[CH2:7]([C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1)[C:8]1[CH:13]=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:29]1([CH:36]=CC(O)=[CH:32][CH:31]=1)[OH:30]>CCOCC.CN(C)C=O.CN(C)P(=O)(N(C)C)N(C)C>[CH2:7]([CH:8]([O:30][C:29]1[CH:31]=[CH:32][C:3]([O:4][CH2:5][CH3:6])=[CH:2][CH:36]=1)[CH3:13])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 5

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 75634-BenzylphenolHCID 11430Potassium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-

Product 1

HCID 68134387HCID 68134387, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

28.2 g of 2-chloroethyl-ethyl ether is added dropwise in the course of one hour at a bath temperature of 105°-110° C, with stirring, to a mixture of 36.8 g of 4-benzylphenol, 40 g of finely pulverised anhydrous potassium carbonate, 0.5 g of potassium iodide, 0.1 g of hydroquinone, 90 ml of hexamethylphosphoric acid triamide and 90 ml of dimethylformamide; and the mixture is held for a further 20 hours at this temperature. In further processing, the cooled reaction mixture is poured into about 800 ml of ice water, and extraction is repeatedly performed with ether. The combined ether phases are washed neutral with 10% potassium hydroxide solution followed by saturated sodium chloride solution; they are then dried over sodium sulphate and treated with active charcoal. After the solvent has been distilled off, the crude product is chromatographed on silica gel (eluant: diethyl ether/hexane 1:4) to yield pure 1-benzyl-4-(2-ethoxy)-ethoxybenzene (nD20 : 1.5502).

Workup

  1. customIn further processing, the cooled reaction mixture
  2. washThe combined ether phases are washed neutral with 10% potassium hydroxide solution
  3. dry with materialthey are then dried over sodium sulphate
  4. additiontreated with active charcoal
  5. distillationAfter the solvent has been distilled off
  6. customthe crude product is chromatographed on silica gel (eluant: diethyl ether/hexane 1:4)

Sources & evidence

ORD record
ord-da30edcf05e44ebb9b4227014b727b3d
Source dataset
uspto-grants-1976_12
Patent number
US03998890

Reaction notes

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