3,4-dihydro-2H-pyran → 3-(Tetrahydro-2H-pyran-2-yloxy)caprylonitrile

HRID 2397610Notes

Reaction equation

HRID 2397610 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:4]#[N:5].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:4]#[N:5]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 134138033-Hydroxycaprylonitrile

Product 1

HCID 234680723-(Tetrahydro-2H-pyran-2-yloxy)caprylonitrileYield 95.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-hydroxycaprylonitrile (5.2 g., 36.8 millimole), dihydropyran (3.8 g., 45 millimole) and p-toluenesulfonic acid. hydrate (catalytic amount) is stirred at 25° C. for 16 hours, then diluted with ether (100 ml.). The resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2 × 25 ml.), dried over magnesium sulfate and filtered. Evaporation of the filtrate in vacuo affords the title compound as a pale yellow oil (7.9 g., 95%), pmr (CDCl 3) δ 0.93 (3H, t), 2.54 (2H, q) and 4.68 (H, m).

Workup

  1. washThe resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2 × 25 ml.)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-a981d10c548e45fabe43299d2f374580
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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