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Hydrochloric Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

HRID 1822342
Notes
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Reaction equation

HRID 1822342 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=1[CH3:24])[CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH3:10])=[CH:19][C:18]=1[CH3:24])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 109535825-Methoxy-2-methylphenolHCID 537177243-(4-Fluoro-2-methyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 690715883-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl esterYield 47.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

The compounds of 5-methoxy-2-methyl-phenol (1.46 g, 9.60 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (1.00 g, 4.80 mmol), potassium carbonate (1.33 g, 9.60 mmol) are dissolved in dimethylsulfoxide (12 mL) under nitrogen, and the mixture is stirred overnight at 140° C. HCl 10% is added, and the mixture is extracted with diethyl ether. The organic layer is washed with water, dried (Na2SO4) and filtered, and then the solvent is evaporated in vacuo. Purification by flash chromatography by eluting with hexane:ethyl acetate 10:1 to afford the title compound (0.74 g, 47%). Rf=0.44 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.34 (t, 3H, J=7.3 Hz), 2.13 (s, 3H), 2.40 (s, 3H), 3.74 (s, 3H), 4.26 (q, 2H, J=7.1 Hz), 6.28 (d, 1H, J=15.9 Hz), 6.53 (d, 1H, J=2.4 Hz), 6.66-6.73 (m, 3H), 7.15 (d, 1H, J=8.3 Hz), 7.51 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=16.0 Hz).

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. washThe organic layer is washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated in vacuo
  6. customPurification by flash chromatography
  7. washby eluting with hexane:ethyl acetate 10:1

Sources & evidence

ORD record
ord-026c8309746a46508710020b08ba8d96
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608639B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes