O-Cresol → 1-(Methoxymethoxy)-2-methylbenzene

HRID 1669460

Reaction equation

HRID 1669460 reaction equation
[H-].[Na+].[C:3]1([CH3:10])[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][CH:4]=1.C[CH2:12][O:13][CH2:14]C.C(Cl)OC>CCOCC.CN(C=O)C.O>[CH3:12][O:13][CH2:14][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:10]

Participants

7

Reactant 4

HCID 335O-CresolHCID 3283Diethyl Ether2×HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 38393511-(Methoxymethoxy)-2-methylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19966313DMF etherSolvent

Procedure

To a suspension of NaH (60% dispersion in mineral oil; 1.2 eq) in Et2O/DMF (5:1, 0.2M) a solution of o-cresol in Et2O (1 eq, 2M) was added dropwise over 15 min. A solution of MOMCl in Et2O (1.1 eq, 2M) was added and the mixture was stirred for 30 min then poured into H2O and extracted with Et2O. The combined organic extracts were washed with 1N NaOH, H2O and brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound. The product was used in the next step without further purification.

Workup

  1. additionwas added dropwise over 15 min
  2. extractionextracted with Et2O
  3. washThe combined organic extracts were washed with 1N NaOH, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-20b43335f7ed4d1abe3450533abe617c
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Linked notes

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