Hydrochloric Acid → HCID 20216757, compound

HRID 236470Notes

Reaction equation

HRID 236470 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

A suspended solution of activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) was stirred under refluxing. 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 under refluxing for 1 hour. Anhydrous conditions were maintained throughout this experiment. The cooled solution was poured into 0.1N hydrochloric acid (5.6 ml) and the resultant solution was adjusted to pH 2.0 with 2N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution 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. temperatureunder refluxing
  2. temperatureunder refluxing for 1 hour
  3. temperatureAnhydrous conditions were maintained throughout this experiment
  4. filtrationThe excess of zinc was filtered off
  5. extractionthe crude products were extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe ethyl acetate was evaporated off under reduced pressure
  9. customto give the crude ester, which
  10. customwas purified by column chromatography on silica gel (Merck)
  11. washeluted with a mixture of cyclohexane and ethyl acetate (19:1)
  12. additionThe fractions containing the object compound
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was dried by high vacuum pump

Sources & evidence

ORD record
ord-7c86a625db724459aff1512e57634117
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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