M-Cresol → 3-(methoxymethoxy)toluene

HRID 2422509Notes

Reaction equation

HRID 2422509 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[H-].[Na+].[CH3:11][O:12][CH2:13]Cl>CN(C=O)C>[CH3:11][O:12][CH2:13][O:7][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:8])[CH:1]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 109647013-(methoxymethoxy)toluene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To m-cresol (19.4 mL, 188 mmol) in DMF (1 L) was added NaH (60% disp. in oil, 9.04 g, 0.226 mmol) in several portions. The mixture was stirred at rt for 30 min, chloromethyl methyl ether (11.5 mL, 151 mmol) was added in one portion, and the reaction mixture was stirred at room temperature overnight, partitioned between 1N aq. NaOH and Et2O. The organic phase was washed with 1N aq. NaOH, dried over MgSO4, filtered and concentrated in vacuo, to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.18 (t, 1H), 6.86-6.77 (m, 3H), 5.18 (s, 2H), 3.43 (s, 3H), 2.29 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. custompartitioned between 1N aq. NaOH and Et2O
  3. washThe organic phase was washed with 1N aq. NaOH
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7dc271f12e14c8ab2089bb87858de1e
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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