3,4-dihydro-2H-pyran → 2H-Pyran, 2-[(5-chloropentyl)oxy]tetrahydro-

HRID 1654295Notes

Reaction equation

HRID 1654295 reaction equation
[CH2:1]([Cl:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][Cl:7]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 789155-Chloro-1-pentanol

Product 1

HCID 1144672H-Pyran, 2-[(5-chloropentyl)oxy]tetrahydro-Yield 62.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of pentamethylene chlorohydrin (10.0 g, 0.0816 mol) in Et2O (165 ml) under nitrogen was treated with 3,4-dihydro-2H-pyran (10.3 g, 0.122 mol) and p-toluenesulfonic acid hydrate (0.5 g) and kept at ambient temperature for 4.5 hours. The mixture was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was distilled to give 4.06 g, bp 79°-82° C. (0.1-0.07 mm Hg) and 10.54 g, bp 82°-84° C. (0.1-0.07 mm Hg) of 5-chloropentyl 2-tetrahydropyranyl ether.

Workup

  1. washThe mixture was washed with aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b3eb007816c34156b30dce6d8f04761a
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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