Hydrochloric Acid → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 1646186Notes

Reaction equation

HRID 1646186 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].Cl.[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:5][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)[CH2:2][C:3]#[CH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OLHCID 516892Sodium Bicarbonate

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-butyn-1-ol (74.5 g, 1.06 mol) in carbon tetrachloride (225 ml) is cooled in an ice bath, and treated with concentrated hydrochloric acid (1 ml). Dihydropyran (157 g, 1.86 mol) is then added via a dropping funnel. After stirring 16 hours the reaction mixture is treated with solid sodium bicarbonate for 30 minutes and filtered. The reaction mixture is concentrated and the residue is distilled in vacuo to give the title compound.

Workup

  1. filtrationfiltered
  2. concentrationThe reaction mixture is concentrated
  3. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-f1c5ff75111c44d3b97182522cd585e5
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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