Benzaldehyde → 1,2-Diphenylethanol

HRID 1596818

Reaction equation

HRID 1596818 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH2:6]([C:13]([OH:22])([C:18]([CH3:21])([CH3:20])C)C(C)(C)C)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)C1C=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>CCCCC.C1COCC1.[Cl-].[Cl-].[Zn+2].C(OCC)C>[C:18]1([CH:13]([OH:22])[CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:20]=[CH:3][CH:2]=[CH:1][CH:21]=1

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 12679HexamethylphosphoramideHCID 125862083-Benzyl-2,2,4,4-tetramethyl-3-pentanolHCID 178418339Butyllithium

Product 1

HCID 941781,2-Diphenylethanol

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1.33 ml of a 1.6-molar solution of n-butyllithium (2.13 mmol) in pentane were added dropwise at room temperature under argon for 2 minutes to a stirred solution of 500 mg (2.13 mmol) 3-benzyl-2,2,4,4-tetramethyl-3-pentanol in 4 ml THF. The solution obtained was stirred for 30 minutes, then 275 μl (2.13 mmol) benzaldehyde, 290 mg (2.13 mmol) ZnCl2 and 2 ml HMPA were added. The reaction mixture was heated to 70° C. and stirred for 4 hours at this temperature. Subsequently, it was cooled to room temperature and processed analogous to Example 1. The raw product obtained was cleaned by means of a silica column with 35% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

Workup

  1. customThe solution obtained
  2. stirringstirred for 4 hours at this temperature
  3. temperatureSubsequently, it was cooled to room temperature
  4. customThe raw product obtained

Sources & evidence

ORD record
ord-da1ceb8825d14792851c1be0ef81b0bf
Source dataset
uspto-grants-2001_09
Patent number
US06291713B1

Linked notes

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