Hydrochloric Acid → HCID 12466080, compound

HRID 1608475Notes

Reaction equation

HRID 1608475 reaction equation
Cl.C([O:6][C:7]1[C:8](=[O:23])[C:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(O)[C:10]=1[O:11]CCCC)CCC.O>C1COCC1>[CH2:17]([C:9]1[C:10](=[O:11])[C:7](=[O:6])[C:8]=1[OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22910855HCID 22910855, compound

Product 1

HCID 12466080HCID 12466080, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6N Hydrochloric acid (150 mL) was added in one portion to a stirred solution of crude 2,3-dibutoxy-4-hexyl-4-hydroxycyclobut-2-en-1-one (15.1 g, prepared in Part A above) in THF (150 mL), and the resultant solution was stirred at room temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure to give a yellow solid. To this solid was added water (100 mL), which was then removed under reduced pressure. Toluene (100 mL) was similarly added and removed under reduced pressure, and then dichloromethane (200 mL) was added to the residue and the resultant solution was filtered and concentrated to produce a yellow oil. Hexanes (200 mL) were added and the resultant solution was cooled to induce crystallization. After recrystallization from hexanes, the desired compound was isolated as tan crystals (4.28 g, 33% yield over Parts A and B). The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give a yellow solid
  3. customwas then removed under reduced pressure
  4. additionToluene (100 mL) was similarly added
  5. customremoved under reduced pressure
  6. additiondichloromethane (200 mL) was added to the residue
  7. filtrationthe resultant solution was filtered
  8. concentrationconcentrated
  9. customto produce a yellow oil
  10. customcrystallization
  11. customAfter recrystallization from hexanes

Sources & evidence

ORD record
ord-3d34f63ceacc4259ade14407e83be0e6
Source dataset
uspto-grants-1995_03
Patent number
US05395736

Reaction notes

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