HCID 54456843, compound → 1-(4-Ethoxyphenyl)-2-methyl-1-penten-3-ol

HRID 1018471Notes

Reaction equation

HRID 1018471 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([CH3:14])[CH:12]=[O:13])=[CH:6][CH:5]=1)[CH3:2].[CH2:15]([Mg]Br)[CH3:16]>C(OCC)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([CH3:14])[CH:12]([OH:13])[CH2:15][CH3:16])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 54456843HCID 54456843, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 700830381-(4-Ethoxyphenyl)-2-methyl-1-penten-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-(4-ethoxyphenyl)-2-methylpropenaldehyde (10 g, 0.053 mol) in dried diethyl ether (150 ml) cooled to −15° C. and stirred under an atmosphere of nitrogen was added a solution of ethylmagnesium bromide in diethylether (3M, 19.3 ml) The reaction mixture was allowed to warm to room temperature and after ½ h poured onto ice cold aqueous hydrochloric acid (2M, 50 ml) and the organic phase washed with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to give 1-(4-ethoxyphenyl)-3-hydroxy-2-methylpent-1-ene as a colourless oil.

Workup

  1. additionpoured onto ice cold aqueous hydrochloric acid (2M, 50 ml)
  2. washthe organic phase washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bcf07f1fbb8c4197af295d40ac748df5
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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