Hydrochloric Acid → HCID 20216757, compound

HRID 1903517Notes

Reaction equation

HRID 1903517 reaction equation
II.Br[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:12][CH:13]([CH3:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[O:26].Cl>O1CCCC1.[Zn]>[OH:26][CH:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([CH3:27])[CH3:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 807IodineHCID 79177tert-Butyl bromoacetateHCID 1108550713-methyltetradecanal

Product 1

HCID 20216757HCID 20216757, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) were stirred and heated under reflux. To the mixture was added a solution of tert-butyl bromoacetate (312 mg) and 13-methyltetradecanal (226 mg) in tetrahydrofuran (3 ml), and the reactants were stirred and heated under reflux for 1 hour. Anhydrous conditions were maintained throughout the experiment. The cooled solution was poured into 0.1 N hydrochloric acid (5.6 ml) and the pH was adjusted to 2.0 with 2 N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate solution was washed with aqueous sodium hydrogen carbonate and brine, and then dried over magnesium sulfate. The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) and eluted with a mixture of cyclohexane and ethyl acetate (19:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was dried by high vacuum pump to afford an oil of tert-butyl 3-hydroxy-15-methylhexadecanoate (180 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. temperatureAnhydrous conditions were maintained throughout the experiment
  6. filtrationThe excess of zinc was filtered off
  7. extractionthe crude products were extracted with ethyl acetate
  8. washThe ethyl acetate solution was washed with aqueous sodium hydrogen carbonate and brine
  9. dry with materialdried over magnesium sulfate
  10. customThe ethyl acetate was evaporated off under reduced pressure
  11. customto give the crude ester, which
  12. customwas purified by column chromatography on silica gel (Merck)
  13. washeluted with a mixture of cyclohexane and ethyl acetate (19:1)
  14. additionThe fractions containing the object compound
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was dried by high vacuum pump

Sources & evidence

ORD record
ord-8c4c9ad1ab0b4e27bbfc9a789c82cbec
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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