Chloromethyl Methyl Ether → 1-Methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene

HRID 716811Notes

Reaction equation

HRID 716811 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:15][O:16][CH3:17]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:13])([CH3:12])[CH2:10][O:11][CH2:15][O:16][CH3:17])[CH:4]=1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 3167872-(3-Methoxyphenyl)-2-methylpropan-1-ol2×

Product 1

HCID 867156941-Methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzeneYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-2-methyl-propan-1-ol (Intermediate 39, 900 mg, 4.99 mmol) in THF (15 mL) sodium hydride 60% dispersion in mineral oil (300 mg, 7.49 mmol) was added and the reaction mixture was stirred for 15 minutes at room temperature. Chloro(methoxy)methane (603.02 mg, 7.49 mmol) was added and the reaction mixture was heated to 55° C. and stirred overnight. The reaction was cooled to 0° C. and quenched with water (10 mL) (added dropwise) and extracted with EtOAc (30 mL). Organics were dried over Na2SO4, filtered and evaporated in vacuo to afford the title compound (525 mg) that was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated to 55° C.
  2. stirringstirred overnight
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with water (10 mL) (
  5. additionadded dropwise) and
  6. extractionextracted with EtOAc (30 mL)
  7. dry with materialOrganics were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6c45ba8746074eaf97a65c02bfcbb785
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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