Chloromethyl Methyl Ether → HCID 22467254, compound

HRID 420549Notes

Reaction equation

HRID 420549 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4](C)[C:5]([OH:8])=[CH:6][CH:7]=1.C(N([CH2:18][CH3:19])C(C)C)(C)C.Cl[CH2:21][O:22]C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH2:18][O:22][CH3:21])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 74075Phenol, chlorodimethyl-HCID 81531Diisopropylethylamine

Product 1

HCID 22467254HCID 22467254, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-chloro-3-methylcresol (15.0 g; 0.105 mol), N,N-diisopropylethylamine (23.3 ml; 0.137 mol) and THF (150 ml), was added dropwise chloromethylmethyl ether (9.50 ml; 0.126 mol) at room temperature. The mixture was stirred at 60° C. for 27.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1) to give 2-chloro-5-(methoxyethoxy)toluene as dark reddish-brown oil (17.7 g; 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-37fdad035ef54979b0d2a6e6ea343cbe
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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