3,4-dihydro-2H-pyran → 2H-Pyran, 2-(4-chlorobutoxy)tetrahydro-

HRID 1534905Notes

Reaction equation

HRID 1534905 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]>Cl>[Cl:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 135694-Chloro-1-butanol

Product 1

HCID 1704882H-Pyran, 2-(4-chlorobutoxy)tetrahydro-Yield 89.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

Dihydropyran (15.5 g) was added dropwise to a mixture of 4-chlorobutanol (20 g) and hydrochloric acid (18M, 1 drop) at RT. The mixture was stirred for 30 min and washed with H2O (100 ml), aqueous NaHCO3 (1M, 50 ml) and BR (50 ml). The dried liquid was heated under reduced pressure to leave the title compound as a colourless liquid (31.9 g). T.l.c. [L] Rf 0.5.

Workup

  1. washwashed with H2O (100 ml), aqueous NaHCO3 (1M, 50 ml) and BR (50 ml)
  2. temperatureThe dried liquid was heated under reduced pressure

Sources & evidence

ORD record
ord-9c17ccaf3c3249dda1617470bc6bbb96
Source dataset
uspto-grants-1992_02
Patent number
US05091422

Reaction notes

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