Water → HCID 54449301, compound

HRID 484988Notes

Reaction equation

HRID 484988 reaction equation
[CH3:1][Mg]I.[CH3:4][C:5]1[CH:10]=[C:9]([O:11]C)[C:8](C)=[CH:7][C:6]=1[CH:14]=[CH:15][C:16](OCC)=O.O.C[CH2:23][O:24][CH2:25][CH3:26]>>[CH3:4][C:5]1[CH:26]=[C:25]([O:24][CH3:23])[C:15]([CH3:16])=[CH:14][C:6]=1[CH:7]=[CH:8][C:9]([CH3:10])([OH:11])[CH3:1]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether2×HCID 53883576HCID 53883576, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 54449301HCID 54449301, compound

Procedure

To 0.3M of methyl magnesium iodide in 100 ml of ether, stirred under a nitrogen atmosphere and in a cooling bath of -5° C., was added dropwise a solution of ethyl 3-(2,5-dimethyl-4-methoxyphenyl)-acrylate (23.4 g, 0.1M) in 50 ml of diethyl ether. This mixture was stirred for 3 hours at room temperature. Cold water (150 ml) was added, and the product was extracted into ether. The ethereal layer was washed with brine, dried (magnesium sulfate) and concentrated on rotary evaporator to give 21.4 g of 4-(2,5-dimethyl-4-methoxyphenyl)-2-methyl-3-buten-2-ol as yellow powder.

Workup

  1. extractionthe product was extracted into ether
  2. washThe ethereal layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated on rotary evaporator

Sources & evidence

ORD record
ord-d473ba330c454954a408c81f44bab263
Source dataset
uspto-grants-1985_08
Patent number
US04534979

Reaction notes

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