Tetrahydrofuran → 1-Bromo-6,7-dihydroxyheptane

HRID 2290249Notes

Reaction equation

HRID 2290249 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[O:9][CH2:8]1.[O:10]1CCCC1.Cl(O)(=O)(=O)=O>O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:9])[CH2:8][OH:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 142253782-(5-Bromopentyl)oxirane

Product 1

HCID 201577701-Bromo-6,7-dihydroxyheptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

42 g of 1-bromo-6,7-epoxyheptane were introduced into a mixture of 400 ml of tetrahydrofuran and 235 ml of water, which had been adjusted to pH 2 with perchloric acid, at room temperature. After stirring at room temperature for 8 hours, the mixture was neutralized, evaporated under reduced pressure and the residue was extracted with methylene chloride. After removal of the solvent, 41.5 g of crude 1-bromo-6,7-dihydroxyheptane were obtained.

Workup

  1. customevaporated under reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. customAfter removal of the solvent

Sources & evidence

ORD record
ord-b75f16bf51384cb1844f353acaa75c3f
Source dataset
uspto-grants-1986_10
Patent number
US04616020

Reaction notes

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