Allyl bromide → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 1907332Notes

Reaction equation

HRID 1907332 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1.[Zn]>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:16][CH:15]=[CH2:14]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 702953-Chloropropiophenone

Product 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-olYield 97.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3-chloro-1-phenylpropan-1-one (100 g, 0.595 mol) in THF (280 ml) was added dropwise to a well-stirred mixture of zinc powder (need not be activated) (40 g, 1.231 mol, satd aq NH4Cl solution (1500 ml) and THF (400 ml). Allyl bromide (143 g, 1.19 mol) was dissolved in THF (200 ml) was slowly added to the reaction mixture. The reaction was mildly exothermic, and the mixture began to reflux spontaneously. After refluxing had ceased, the mixture was stirred for 1 h. The mixture was extracted with EtOAc, dried over anhydrous Na2SO4, and concentrated to give 1-chloro-3-phenylhex-5-en-3-ol (122 g, 97%). 1H NMR: (400 MHz, CDCl3): δ=2.24 (s, 1H), 2.34 (m, 2H), 2.53 (m, 1H), 2.75 (m, 1H), 3.20 (m, 1H), 3.58 (m, 1H), 5.18 (t, 1H), 5.51 (m, 1H), 7.26 (m, 1H), 7.26-7.39 (m, 3H).

Workup

  1. additionwas slowly added to the reaction mixture
  2. temperatureto reflux spontaneously
  3. temperatureAfter refluxing
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d8a735b176c4260b715f86c828a18a2
Source dataset
uspto-grants-2013_12
Patent number
US08598163B2

Reaction notes

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