Water → HCID 19849494, compound

HRID 652116Notes

Reaction equation

HRID 652116 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][C:18]#[C:19][CH2:20]Br.O>C(O)C>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][C:18]#[C:19][CH2:20][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 14798Sodium HydroxideHCID 113682802-(4-Bromobut-2-ynoxy)tetrahydropyran

Product 1

HCID 19849494HCID 19849494, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.35 g (0.025 mol) of phenol in 20 ml of absolute ethanol, there was added 1.10 g (0.0275 mol) of sodium hydroxide. The mixture was refluxed until complete disolution and 2.92 g (0.0125 mol) of 1-bromobut-2-yn-4-ol tetrahydropyranyl ether were added, and the reflux resumed for 2 additional hours. It was then cooled, poured into water and extracted with ether. The organic extracts were washed with 20% aqueous sodium hydroxide solution and water, dried and evaporated in vacuo. The residue was purified by column chromatography on 50 g of silica gel, using hexane-ethyl acetate (98:2) as eluant, to yield 4-phenoxybut-2-yn-1-ol tetrahydropyranyl ether, as an oil.

Workup

  1. additionwere added
  2. temperatureIt was then cooled
  3. extractionextracted with ether
  4. washThe organic extracts were washed with 20% aqueous sodium hydroxide solution and water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on 50 g of silica gel

Sources & evidence

ORD record
ord-60bcbfad883c439486c92c9c771acc29
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Reaction notes

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