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

HRID 363518

Reaction equation

HRID 363518 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-8effe885a6cc489eb381db367714b7e9
Source dataset
uspto-grants-1999_02
Patent number
US05874475

Linked notes

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