3,4-dihydro-2H-pyran → 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

HRID 1352178Notes

Reaction equation

HRID 1352178 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

Participants

3

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 779706-Bromo-1-hexanol

Product 1

HCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranYield 90.9%

Procedure

197.8 g (1.09 mol) 6-bromo-1-hexanol were given into a 500 ml reactor vessel and cooled to 5° C. or less. 102.1 g (1.21 mol) dihydropyran were added dropwise to this at a temperature of 10° C. or less. After dropping was finished, the mixture was returned to room temperature and stirred for one hour. The precipitate obtained in the reaction was purified in a silica gel column with hexane/IPE (diusopropyl ether)=5/1, resulting in 263.4 g of 6-bromo-1-(tetrahydropyranyloxy)hexane. The yield was 90.9%. The chemical formula for the reaction formula of Step 1 is shown below in equation (2).

Workup

  1. temperaturecooled to 5° C. or less
  2. customwas returned to room temperature
  3. customThe precipitate obtained in the reaction
  4. customwas purified in a silica gel column with hexane/IPE (diusopropyl ether)=5/1
  5. customresulting in 263.4 g of 6-bromo-1-(tetrahydropyranyloxy)hexane

Sources & evidence

ORD record
ord-6d0f5cae99de4d2c9b7843c6df198e31
Source dataset
uspto-grants-2007_05
Patent number
US07220468B2

Reaction notes

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