Chloromethyl Methyl Ether → HCID 90025785, compound

HRID 1506947Notes

Reaction equation

HRID 1506947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH2:10][OH:11].C(N(C(C)C)CC)(C)C.Cl[CH2:22][O:23][CH3:24]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH2:10][O:11][CH2:22][O:23][CH3:24]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11557356(2E)-3-(2-Chlorophenyl)-2-propen-1-ol

Product 1

HCID 90025785HCID 90025785, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 ml round-bottomed flask, (E)-3-(2-chlorophenyl)prop-2-en-1-ol (2.96 g, 17.5 mmol, Preparation example 1) and Dichloromethane (17.5 ml) were added and the reaction mixture was cooled to 0° C. Diisopropylethylamine (6.1 ml, 35.1 mmol) was added and stirred at 0° C. Methyl chloromethyl ether (2.77 ml, 35.1 mmol) was added dropwise and stirred for overnight. The reaction mixture was quenched with 1N NaOH solution, extracted by dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under vacuum. The crude compound was purified by a silica gel column to produce the title compound (3.43 g, 85˜95%).

Workup

  1. stirringstirred for overnight
  2. customThe reaction mixture was quenched with 1N NaOH solution
  3. extractionextracted by dichloromethane
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-3232505a1a3e4e0bb30364d800f16c4e
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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