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

HRID 228140Notes

Reaction equation

HRID 228140 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 91.1%

Procedure

First, 197.8 g (1.09 mol) of 6-bromo-1-hexanol were fed into a 500 mL reactor vessel and cooled to 5° C. or less, and further 102.1 g (1.21 mol) of dihydropyran were dripped at a temperature of 10° C. or less. After completion of dripping, the mixture was warmed to room temperature to carry out a reaction under stirring for one hour. Residues obtained by this reaction were purified by silica gel column with hexane/IPE (diisopropylether)=5/1, and thus 263.4 g of 6-bromo-1-(tetrahydropyranyloxy)hexane were obtained. The yield was 90.9%. Formula (26) below shows the reaction formula of the step 1.

Workup

  1. temperaturecooled to 5° C. or less
  2. customwere dripped at a temperature of 10° C. or less
  3. customa reaction
  4. customResidues obtained by this reaction
  5. customwere purified by silica gel column with hexane/IPE (diisopropylether)=5/1

Sources & evidence

ORD record
ord-64bb2ba12ad44990b796d89a7af372cf
Source dataset
uspto-grants-2009_07
Patent number
US07560731B2

Reaction notes

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