Ammonium Chloride → 1-Chlor-5-methyl-3-phenylhex-5-en-3-ol

HRID 1422643Notes

Reaction equation

HRID 1422643 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-].I[CH2:15][C:16]([CH3:18])=[CH2:17]>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])[CH2:17][C:16]([CH3:18])=[CH2:15]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 702953-Chloropropiophenone2×HCID 108777523-Iodo-2-methylprop-1-ene2×

Product 1

HCID 595323881-Chlor-5-methyl-3-phenylhex-5-en-3-olYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 3-chloro-1-phenylpropan-1-one (16.8 g, 0.1 mol) in THF (50 mL) was added to a well-stirred suspension of zinc powder (13 g, 0.2 mol) in a mixture of satd aq NH4Cl solution (260 mL) and THF (65 mL). A solution of 3-iodo-2-methylprop-1-ene (36.4 g, 0.2 mol) in THF (50 mL) was added dropwise. The reaction was mildly exothermic, and the mixture began to reflux spontaneously. After refluxing had ceased, the mixture was stirred for 1 h. TLC showed the 3-chloro-1-phenylpropan-1-one had not reacted completely. A solution of 3-iodo-2-methylprop-1-ene (18.2 g, 0.1 mol) in THF (30 mL) was added, and the mixture was stirred at rt overnight. The mixture was extracted with EtOAc (2×500 mL). The combined organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with petroleum ether/EtOAc 50:1→30:1→5:1, to give 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (17 g, yield 76%) as an oil.

Workup

  1. temperatureto reflux spontaneously
  2. temperatureAfter refluxing
  3. customhad not reacted completely
  4. stirringthe mixture was stirred at rt overnight
  5. extractionThe mixture was extracted with EtOAc (2×500 mL)
  6. customThe combined organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluted with petroleum ether/EtOAc 50:1→30:1→5:1

Sources & evidence

ORD record
ord-f85d6609e0a34e29967963e1ec6cf535
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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