tert-Butanol → HCID 11746573, compound

HRID 1585251Notes

Reaction equation

HRID 1585251 reaction equation
Cl[C:2]1C=C(Cl)C=[C:7](Cl)[C:3]=1[C:4](Cl)=O.[C:13]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.CC(O)(C)C>CN(C1C=CN=CC=1)C.C1C=CC=CC=1.C1COCC1>[C:13]([CH2:21][CH2:22][C:23]([O:25][C:3]([CH3:7])([CH3:4])[CH3:2])=[O:24])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 728713-Benzoylpropionic acid2×HCID 27337032,4,6-Trichlorobenzoyl chloride

Product 1

HCID 11746573HCID 11746573, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 500 mL round bottom flask was added 10.40 g (0.0426 mol) of 2,4,6-trichlorobenzoyl chloride. To this was added 300 mL of THF followed by 7.65 g (0.0429 mol) of 3-benzoylpropionic acid (I). Once the 3-benzoylpropionic acid had dissolved, then 6.1 mL (0.0830 mol) of triethylamine was added. The solution was stirred for 6 hours, after which the THF solution was filtered to remove the triethylamine hydrochloride. The filtrate was rotoevaporated to yield a light beige solid. To this solid was added 200 mL of benzene followed by 6.0 mL (0.104 mol) of 2-methyl-2-propanol and the mixture was stirred with heating to dissolve all of the solid. After complete dissolution, 5.40 g (0.0442 mol) of DMAP was added to the solution. The solution immediately turned dark red and was stirred at room temperature for 36 hours. The solution was washed with 10% aqueous HCl solution, followed by 2×5% aq. NaOH solution and finally with water. The organic layer was then dried (MgSO4), filtered and concentrated. The resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes) and the resultant oil obtained was distilled under reduced pressure to yield 6.45 g (64%) of t-butyl 3-benzoylpropionate as a colorless oil.

Workup

  1. filtrationafter which the THF solution was filtered
  2. customto remove the triethylamine hydrochloride
  3. customto yield a light beige solid
  4. stirringthe mixture was stirred
  5. temperaturewith heating
  6. dissolutionto dissolve all of the solid
  7. additionwas added to the solution
  8. stirringThe solution immediately turned dark red and was stirred at room temperature for 36 hours
  9. washThe solution was washed with 10% aqueous HCl solution
  10. dry with materialThe organic layer was then dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes)
  14. customthe resultant oil obtained
  15. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-4c2702103c0744fe9313d8612023cd9b
Source dataset
uspto-grants-1999_08
Patent number
US05936124

Reaction notes

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