Hydrochloric Acid → Tetrahydropyranyl bromomethyl-cyclohexyl ether

HRID 1289350Notes

Reaction equation

HRID 1289350 reaction equation
[Br:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6](O)[CH2:5][CH2:4]1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.Cl.C(=O)([O-])[O-:18].[K+].[K+]>>[Br:1][CH2:2][C:3]1([O:18][CH:15]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 218327074-(Bromomethyl)cyclohexan-1-ol

Product 1

HCID 21832708Tetrahydropyranyl bromomethyl-cyclohexyl ether

Procedure

4-Bromomethylcyclohexanol (C-5) (3.0 g) and dihydropyran (2.6 g) were mixed together and cooled with ice. A tiny drop of 10% hydrochloric acid was added. Exothermic reaction occurred and stirred at ambient temperature overnight. The solution was neutralized with potassium carbonate and extracted with dichloromethane (50 ml). It was filtered and then dichloromethane from the filtrate was evaporated to yield the compound C-6, tetrahydropyranyl bromomethyl-cyclohexyl ether (5.0 g).

Workup

  1. temperaturecooled with ice
  2. customExothermic reaction
  3. extractionextracted with dichloromethane (50 ml)
  4. filtrationIt was filtered
  5. customdichloromethane from the filtrate was evaporated

Sources & evidence

ORD record
ord-8e0dbd93b09048068e94346ed1706d6b
Source dataset
uspto-grants-1998_05
Patent number
US05750300

Reaction notes

Loading…