p-METHOXY-alpha-METHYLCINNAMALDEHYDE → 3-Hydroxy-1-(4-methoxyphenyl)-2-methylpent-1-ene

HRID 1018468Notes

Reaction equation

HRID 1018468 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([CH3:13])[CH:11]=[O:12])=[CH:5][CH:4]=1.[CH2:14]([Mg]Br)[CH3:15]>C(OCC)C>[OH:12][CH:11]([CH2:14][CH3:15])[C:10]([CH3:13])=[CH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 228993p-METHOXY-alpha-METHYLCINNAMALDEHYDEHCID 178418443HCID 178418443, compound

Product 1

HCID 700839453-Hydroxy-1-(4-methoxyphenyl)-2-methylpent-1-ene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-(4-methoxyphenyl)-2-methylpropenaldehyde (10.3 g, 0.058 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, 21.4 ml). The reaction mixture was allowed to warm to room temperature and after ½ hour poured onto ice cold aqueous hydrochloric acid (2M, 50 ml). The organic phase was separated, washed with water, a saturated solution of sodium bicarbonate and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to give 3-hydroxy-1-(4-methoxyphenyl)-2-methylpent-1-ene as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-954cadaa276849109d5b6e6def463274
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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