Potassium Carbonate → Ethyl 2-(3-(2,6-dimethybenzyloxy)-4-methylphenyl)acetate

HRID 516863

Reaction equation

HRID 516863 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24][O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 21079755Ethyl 3-hydroxy-4-methylphenylacetate

Product 1

HCID 66899575Ethyl 2-(3-(2,6-dimethybenzyloxy)-4-methylphenyl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Ethyl 2-(3-hydroxy-4-methylphenyl)acetate (Step C, 1.84 g, 9.5 mmol), K2CO3 (1.96 g, 14.2 mmol) in DMF (10 ml) was added 2,6-Dimethylbenzyl chloride (1.61 g, 10.4 mmol) at room temperature under argon. The reaction mixture was stirred for 16 hours at the room temperature, diluted with ethyl acetate and washed with water (2×), and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hexane:ethyl acetate, 4:1) to give the title compound.

Workup

  1. washwashed with water (2×), and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-4f74d5a260b84d35bd425753e3e4ef3c
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Linked notes

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