Phenethyl bromide → HCID 15524231, compound

HRID 481161Notes

Reaction equation

HRID 481161 reaction equation
[C:1]1([CH2:7][CH2:8]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[Cl-].[NH4+]>CCOCC>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]([OH:17])[CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 115693-MethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 15524231HCID 15524231, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
40 °C

Procedure

19.1 ml (0.14 mole) of 2-phenylethyl bromide were dissolved in 100 ml of ether and added dropwise to a suspension of 3.4 g (0.14 mole) of magnesium in 300 ml of ether. The reaction solution was next stirred for one hour at 40° C. and then cooled to 0° C. 20.4 g (0.15 mole) of 3-methoxybenzaldehyde in 100 ml of ether were added while cooling with ice and the reaction solution was stirred overnight at 20° C. 150 ml of a 20% ammonium chloride solution was then added at 0° C. to the reaction solution. The reaction solution was extracted three times with 200 ml of ether each time and the combined ether extracts were dried over sodium sulfate. The solvent was removed in vacuo. After drying, 28.5 g (98%) of 1-(3-methoxyphenyl)-3-phenylpropan-1-ol were obtained as a grey oil.

Workup

  1. temperaturecooled to 0° C
  2. temperaturewhile cooling with ice
  3. stirringthe reaction solution was stirred overnight at 20° C
  4. extractionThe reaction solution was extracted three times with 200 ml of ether each time
  5. dry with materialthe combined ether extracts were dried over sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customAfter drying

Sources & evidence

ORD record
ord-d16b258bb0224e58b8f3c0141fa9f628
Source dataset
uspto-grants-2003_11
Patent number
US06653508B2

Reaction notes

Loading…