Water → HCID 67289107, compound

HRID 879958Notes

Reaction equation

HRID 879958 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12]Cl.[CH:14]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:16][CH2:15]1.O>C(Cl)Cl>[CH:14]1([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:10][O:11][CH3:12])=[CH:19][CH:18]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 109862774-cyclopropylphenol

Product 1

HCID 67289107HCID 67289107, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (77.6 mL) and chloromethyl methyl ether (33.7 mL) were added to a solution of 4-cyclopropylphenol (24.0 g) in methylene chloride (250 mL) 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 a 1 mol/L sodium hydroxide aqueous solution, 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 to obtain the target product (27.6 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 a 1 mol/L sodium hydroxide aqueous solution, 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

Sources & evidence

ORD record
ord-72f687b098f048b3beded5332eed8b82
Source dataset
uspto-grants-2015_03
Patent number
US08993543B2

Reaction notes

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