2,6-Dimethoxyphenol → HCID 67464460, compound

HRID 2171207Notes

Reaction equation

HRID 2171207 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20]1[CH2:22][CH2:21]1>C(#N)C>[CH:20]1([CH2:19][O:11][C:4]2[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 70412,6-DimethoxyphenolHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 67464460HCID 67464460, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 2,6-dimethoxyphenol (2 g, 12.9 mmol) in acetonitrile (50 mL) was added potassium carbonate (3.5 g, 25.8 mmol) and (bromomethyl)cyclopropane (3.5 g, 25.8 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) to afford 2-(Cyclopropylmethoxy)-1,3-dimethoxybenzene as a solid (2 g, 74%).

Workup

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (silica gel, 0-10% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-86ddc088976b489db2549157a839deba
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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