Phenethyl bromide → 1,5-Diphenylpentan-3-ol

HRID 1066868Notes

Reaction equation

HRID 1066868 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Mg].[C:11]1([CH2:17][CH2:18][CH:19]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C>[C:4]1([CH2:3][CH2:2][CH:19]([OH:20])[CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 7707BenzenepropanalHCID 5462224Magnesium

Product 1

HCID 128385101,5-Diphenylpentan-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 2-(bromoethyl)benzene (1.73 g; 9.33 mmol) in diethylether (10 mL) was added to a stirred slurry of magnesium turnings (250 mg; 10.18 mmol) in 5 mL of ether. The reaction was initiated with a heat gun, and after the addition was complete the mixture was heated on an oil bath for 30 minutes. 3-Phenyl-1-propanal (1.25 g; 9.33 mmol) was added in 10 mL of ether, and reflux was continued for 1 hour. The reaction was cooled and quenched with saturated ammonium chloride, extracted into 2x ethyl acetate, and the combined organic portions were dried and concentrated. Chromatographic purification on a silica gel column (10% ethyl acetate in hexane) delivered 1.42 g (63%) of the diphenyl alcohol, 1H NMR (300 MHz, CDCl3): δ 1.84 (m, 4H); 2.61-2.76 (m,4H); 3.65 (m, 1H); 7.19-7.29 (m, 10H).

Workup

  1. additionafter the addition
  2. temperaturewas heated on an oil bath for 30 minutes
  3. temperaturereflux
  4. temperatureThe reaction was cooled
  5. customquenched with saturated ammonium chloride
  6. extractionextracted into 2x ethyl acetate
  7. customthe combined organic portions were dried
  8. concentrationconcentrated
  9. customChromatographic purification on a silica gel column (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-942a4896d66341bf98dce6c2f18dee26
Source dataset
uspto-grants-2001_06
Patent number
US06245783B1

Reaction notes

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