Bicarbonate Ion → 2-(3-Bromopropoxy)tetrahydro-2H-pyran

HRID 1656309Notes

Reaction equation

HRID 1656309 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C(=O)(O)[O-]>C(OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 80803,4-dihydro-2H-pyranHCID 123083-Bromo-1-propanol

Product 1

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 35 g (0.251 mol) of 3-bromopropanol and 1 g of p-toluenesulphonic acid in 500 ml of diethylether, 32.5 ml (0.357 mol) of 3,4-dihydro-2H-pyran is added dropwise under cooling with ice water and the solution is stirred for 2 hours at room temperature. The mixture is neutralized with saturated aqueous bicarbonate. washed with brine and concentrated after drying, affording 56 g of 2-(3-bromopropyloxy)tetrahydropyran in practically quantitative yield as a viscous liquid, which may be used without further purification. (C8H15BrO2 ; F.W. 223.1).

Workup

  1. washwashed with brine
  2. concentrationconcentrated
  3. customafter drying

Sources & evidence

ORD record
ord-499ca0f5fdef4b5c99e1f509788f1ea5
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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