3-Phenylprop-2-En-1-Ol → Benzenepropanol

HRID 541172Notes

Reaction equation

HRID 541172 reaction equation
[C:1]1([CH:7]=[CH:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3083-Phenylprop-2-En-1-OlHCID 962Water

Product 1

HCID 31234BenzenepropanolYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

67.1 mg (0.50 mmol) of 3-phenyl-2-propen-1-ol (34), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 6 hours at 800 rpm (reversed every 30 minutes). After the lapse of 6 hours, 10 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 64.7 mg (0.475 mmol) of 3-phenyl-1-propanol (35). The yield was 95%. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 6 hours
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-e561ebc57a1d46ff846767fd168f87ca
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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