Benzaldehyde → 1-Phenylbut-3-en-1-ol

HRID 1532956Notes

Reaction equation

HRID 1532956 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](Br)[CH:10]=[CH2:11].C1COCC1>[NH4+].[Cl-].CCOCC.[Zn]>[C:2]1([CH:1]([OH:8])[CH2:11][CH:10]=[CH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 7841Allyl bromideHCID 8028Tetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Procedure

39 g (0.6 mol) of zinc powder were added at 0° C., a little at a time, to a solution of 53 g (0.5 mol) of benzaldehyde and 73 g (0.6 mol) of allyl bromide in 500 ml of saturated NH4Cl solution/100 ml of THF. The mixture was stirred for 4 hours at room temperature and diluted with ether, and the solid constituents were filtered off with suction. After washing with ether, the phases were separated, and the organic phase was washed with water (2×) and saturated NaCl solution. Drying and concentrating gave 65.2 g (88% of theory) of a colorless oil which was further employed directly.

Workup

  1. filtrationthe solid constituents were filtered off with suction
  2. washAfter washing with ether
  3. customthe phases were separated
  4. washthe organic phase was washed with water (2×) and saturated NaCl solution
  5. customDrying
  6. concentrationconcentrating
  7. customgave 65.2 g (88% of theory) of a colorless oil which

Sources & evidence

ORD record
ord-8acf54bbeb6b45ef9914e22721e0adc5
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Reaction notes

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