Hydrochloric Acid → HCID 69111235, compound

HRID 2214324Notes

Reaction equation

HRID 2214324 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])=[CH:15][CH:14]=1.Cl>C(OCC)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 69111614(2S)-1-(4-Methoxyphenyl)-2-phenylpropan-1-one

Product 1

HCID 69111235HCID 69111235, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Employing a 2 L four-necked flask equipped with a condenser tube, 7.25 g of lithium aluminum hydride was stirred in 290 mL of diethyl ether for 5 minutes. Then, 25.48 g of aluminum chloride as a 280 mL of diethyl ether solution was dropwise added thereto while cooling with ice. After stirring for 5 minutes, 38.26 g of (S)-(+)-1-(4-methoxyphenyl)-2-phenylpropane-1-one as a 245 mL diethyl ether solution was dropwise added thereto. Then, reflux under heating was carried out for 3 hours. After cooling to 0° C., treatment with diluted hydrochloric acid was carried out, extraction with diethyl ether was carried out for liquid separation, and drying over anhydrous sodium sulfate was carried out overnight. After the solvent was distilled off, purification by column chromatography (developing solvent: hexane) was carried out to obtain 30.55 g of (R)-(−)-1-(4-methoxyphenyl)-2-phenylpropane [H-Ph-CH(CH3)—CH2-Ph-OCH3] (yield: 85%).

Workup

  1. customequipped with a condenser tube
  2. temperaturewhile cooling with ice
  3. temperatureThen, reflux
  4. temperatureunder heating
  5. waitwas carried out for 3 hours
  6. extractionextraction with diethyl ether
  7. customwas carried out for liquid separation
  8. dry with materialdrying over anhydrous sodium sulfate
  9. waitwas carried out overnight
  10. distillationAfter the solvent was distilled off
  11. custompurification by column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-90b142edeebd44f78dfae3f766047963
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Reaction notes

Loading…