Ethanol → 5-phenyl-4-pentyn-1-ol

HRID 1722216Notes

Reaction equation

HRID 1722216 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH2:11][O:12]C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 539444652-[(5-Phenylpent-4-yn-1-yl)oxy]oxane

Product 1

HCID 111374345-phenyl-4-pentyn-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-phenyl-5-tetrahydropyranyloxypent-1-yne (0.2 g), absolute ethanol (4 ml) and p-toluenesulphonic acid (20 mg) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (40 ml) and extracted with ether (2×20 ml). The ether extracts were washed with saturated NaHCO3 solution, dried over MgSO4 and purified by chromatography on silica (20 g), eluting with 10% ether in hexane grading to 100% ether, followed by 10% ether acetate in ether. The solvent was removed to give 5-phenylpent-4-yn-1-ol as a colourless oil.

Workup

  1. extractionextracted with ether (2×20 ml)
  2. washThe ether extracts were washed with saturated NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. custompurified by chromatography on silica (20 g)
  5. washeluting with 10% ether in hexane grading to 100% ether
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6df700751b734b82a680b0fda4d41af5
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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