Benzaldehyde → 1-Phenylbut-3-en-1-ol

HRID 1596811Notes

Reaction equation

HRID 1596811 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.CC([C:9]([CH:14]([CH3:16])[CH3:15])([OH:13])[CH2:10][CH:11]=[CH2:12])C.C(=O)C1C=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>CCCCC.C1COCC1.[Zn+2].[Br-].[Br-].C(OCC)C>[C:14]1([CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12])[CH:15]=[CH:3][CH:2]=[CH:1][CH:16]=1

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 12679HexamethylphosphoramideHCID 11321091HCID 11321091, compoundHCID 178418339Butyllithium

Product 1

HCID 2201191-Phenylbut-3-en-1-ol

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.29 ml of a 1.4-molar solution of n-butyllithium (3.20 mmol) in pentane were added dropwise at 0° C. under argon for 2 minutes to a stirred solution of 500 mg (3.20 mmol) 2-methyl-3-isopropyl-hex-5-en-3-ol in 2 ml THF. The solution obtained was heated to room temperature, stirred for 15 minutes, and then a solution of 721 mg (3.20 mmol) ZnBr2 in 2 ml THF and subsequently 330 μl (3.20 mmol) benzaldehyde and 6 ml HMPA were added. The reaction mixture was heated to 70° C. and stirred for 6 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 15% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

Workup

  1. customThe solution obtained
  2. temperatureThe reaction mixture was heated to 70° C.
  3. stirringstirred for 6 hours at this temperature
  4. temperatureSubsequently, it was cooled to room temperature
  5. customThe raw product obtained

Sources & evidence

ORD record
ord-5e23bde5f70740e08b8502fd5d60c24c
Source dataset
uspto-grants-2001_09
Patent number
US06291713B1

Reaction notes

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