3-Chloro-2-methyl-1-propene → HCID 19087772, compound

HRID 1464369Notes

Reaction equation

HRID 1464369 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:18](Cl)[C:19](=[CH2:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)[C:19](=[CH2:18])[CH3:21]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 14674859HCID 14674859, compound

Product 1

HCID 19087772HCID 19087772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g (0.043 mol) of methyl 2-(4-hydroxyphenyl)-2-cyclopentyl-acetate are dissolved in 200 ml of dimethylformamide and 4.1 g (0.043 mol) of methallyl chloride and 5.9 (0.043 mol) of potassium carbonate are added with stirring. The mixture is allowed to react overnight at 100° C. After cooling, the solvent is evaporated in vacuo, the residue is taken up in 200 ml of dichloromethane, the solution is washed twice with 100 ml of water, the organic phase is dried using sodium sulphate and the product from evaporation in vacuo is purified by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=100:5).

Workup

  1. customto react overnight at 100° C
  2. temperatureAfter cooling
  3. customthe solvent is evaporated in vacuo
  4. washthe solution is washed twice with 100 ml of water
  5. customthe organic phase is dried
  6. customthe product from evaporation in vacuo
  7. customis purified by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=100:5)

Sources & evidence

ORD record
ord-acbc824243584adab60a70c10788004e
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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