Hydrogen Bromide → Isopropyl 6-bromohexanoate

HRID 845468Notes

Reaction equation

HRID 845468 reaction equation
[C:1]1(=O)[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:9].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH3:20][CH:21]([OH:23])[CH3:22]>O>[Br:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:23][CH:21]([CH3:22])[CH3:20])=[O:7]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 10401epsilon-CAPROLACTONEHCID 516892Sodium Bicarbonate

Product 1

HCID 549816Isopropyl 6-bromohexanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ε-caprolactone (30 g) in 2-propanol (250 ml) at 0° C. was saturated with hydrogen bromide gas. Sulphuric acid (18M, 5 ml) was then added and the solution was heated under reflux for 16 hours. The reaction mixture was poured into water (200 ml), basified with sodium hydrogen carbonate, and extracted with diethyl ether. The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (alumina, dichloromethane) to give isopropyl 6-bromohexanoate as a pale-yellow oil.

Workup

  1. customat 0° C.
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 16 hours
  4. extractionextracted with diethyl ether
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe solvent was evaporated off under reduced pressure
  7. customto give the crude product which
  8. customwas purified by column chromatography (alumina, dichloromethane)

Sources & evidence

ORD record
ord-daeeacfc4e1844beaeb59c848942492c
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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