Chloromethyl Methyl Ether → 1-Methoxymethoxy-2-(trifluoromethyl)benzene

HRID 1913289Notes

Reaction equation

HRID 1913289 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl>ClCCl.CC(OC)(C)C>[CH3:21][O:22][CH2:23][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 679582-TrifluoromethylphenolHCID 81531Diisopropylethylamine

Product 1

HCID 109436391-Methoxymethoxy-2-(trifluoromethyl)benzeneYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 2-(trifluoromethyl)phenol (12.0 g, 74.0 mmol) in dichloromethane (49 mL) was cooled to 5° C., and N,N-diisopropylethylamine (25.9 mL, 148 mmol) and methoxymethyl chloride (8.43 mL, 111 mmol) were added dropwise, keeping the internal temperature ≦15° C. After stirring for 15 min at ambient temperature, the reaction mixture was diluted with MTBE (250 mL) and washed with 2N HCl (2×50 mL), water (50 mL), 2N NaOH (2×30 mL), water (30 mL), and brine (30 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give the title compound (14.1 g, 68.4 mmol, 92%) which was used without further purification. MS (DCI/NH3) m/z 207 (M+H)+.

Workup

  1. customthe internal temperature ≦15° C
  2. washwashed with 2N HCl (2×50 mL), water (50 mL), 2N NaOH (2×30 mL), water (30 mL), and brine (30 mL)
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db163e0e4ed547e8a1e14cef54b5c0f2
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

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