Water → HCID 67286728, compound

HRID 1045325Notes

Reaction equation

HRID 1045325 reaction equation
C(N(C(C)C)C(C)C)C.[CH3:10][O:11][CH2:12]Cl.[CH2:14]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH2:15][CH3:16].O>C(Cl)Cl>[CH3:10][O:11][CH2:12][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 125804-PropylphenolHCID 81531Diisopropylethylamine

Product 1

HCID 67286728HCID 67286728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyldiisopropylamine (10.3 mL) and chloromethyl methyl ether (4.5 mL) were added to a solution of 4-propylphenol (4.09 g) in methylene chloride (60 mL) under ice cooling to form a reaction solution. This reaction solution was stirred for 15 minutes under ice cooling, and then left overnight at normal temperature. Water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the target product (4.50 g) as a colorless oil.

Workup

  1. customto form a reaction solution
  2. waitleft overnight at normal temperature
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe anhydrous sodium sulfate was removed by filtration
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3093f53611a54c14b2c14477c11b7392
Source dataset
uspto-grants-2013_10
Patent number
US08569270B2

Reaction notes

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