Chloromethyl Methyl Ether → 1-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone

HRID 1295993Notes

Reaction equation

HRID 1295993 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([C:14]1[CH:15]=[C:16]([C:24](=[O:26])[CH3:25])[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[C:19]=1[OH:20])([CH3:13])([CH3:12])[CH3:11].[CH3:27][O:28][CH2:29]Cl>O1CCCC1>[C:10]([C:14]1[CH:15]=[C:16]([C:24](=[O:26])[CH3:25])[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[C:19]=1[O:20][CH2:27][O:28][CH3:29])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 229297281-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone

Product 1

HCID 589099361-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanoneYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (65 ml, 373 mmol) was added to a solution of 1-[3-(tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone (58.6 g, 247 mmol) in tetrahydrofuran (350 ml) under a nitrogen atmosphere while cooling on ice, and then chloromethyl methyl ether (24.5 ml, 322 mmol) was added dropwise. After stirring at the same temperature for 30 minutes, ice water (250 ml) was added and extraction was performed twice with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure to yield the title compound (69.4 g, 99.9% yield) as a light brown oil. This was used without purification for the following reaction.

Workup

  1. temperaturewhile cooling on ice
  2. extractionextraction
  3. washThe organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6f94ca097aa34d8099120646fbf80039
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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