Tetrahydrofuran → 4-Phenylbut-3-en-2-ol

HRID 248659

Reaction equation

HRID 248659 reaction equation
[CH:1](=[CH:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1>CO>[C:2]1([CH:1]=[CH:8][CH:9]([OH:11])[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 151724-Phenylbut-3-en-2-olYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 200 ml stainless steel autoclave were charged 5 g (34.2 mmole) of benzalacetone and 0.213 g (0.171 mmole) of ##STR24## synthesized in Example 4, and 3 ml of tetrahydrofuran and 2 ml of methanol were added thereto, followed by allowing the mixture to react at 30° C. under a hydrogen pressure of 50 kg/cm2 for 45 hours. The solvent was removed by distillation under reduced pressure (10 mmHg), and the reaction product was analyzed by GLC (PEG HT, 25 m, produced by Gasukuro Kogyo K.K.) to find the conversion to be 34.5%. The product was separated into the unreacted ketone and the hydrogenation product by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 by volume) to obtain 1.73 g of 4-phenyl-3-buten-2-ol having a purity of 89%. [α]D25 : +18.1° (c=5, CS2).

Workup

  1. additionwere added
  2. customto react at 30° C. under a hydrogen pressure of 50 kg/cm2 for 45 hours
  3. customThe solvent was removed by distillation under reduced pressure (10 mmHg)
  4. customthe reaction product was analyzed by GLC (PEG HT, 25 m, produced by Gasukuro Kogyo K.K.)
  5. customThe product was separated into the unreacted ketone

Sources & evidence

ORD record
ord-b002e14e106a49858d8bd9cb36bb48ea
Source dataset
uspto-grants-1993_05
Patent number
US05210332

Linked notes

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