Pyrogallol → HCID 1617940, compound

HRID 1787956Notes

Reaction equation

HRID 1787956 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([CH:18]=[CH:17][CH:16]=[C:14]([OH:15])[C:12]=1[OH:13])[OH:11].C(Cl)Cl>C(N(CC)CC)C.O1CCCC1>[C:1]([O:11][C:10]1[CH:18]=[CH:17][CH:16]=[C:14]([O:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12]=1[O:13][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1057PyrogallolHCID 6344DichloromethaneHCID 7412Benzoyl chloride

Product 1

HCID 1617940HCID 1617940, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

A 500 ml three-necked round-bottom flask equipped with a magnetic stirrer was charged with 20.0 g (0.142 mol) of benzoyl chloride, 6.2 g (0.05 mol) of pyrogallol, 400 ml of methylene chloride, and 50 ml of tetrahydrofuran (THF). Triethylamine (TEA; 15.3 g, 0.15 mol) was added drop-wise via an addition funnel over a period of 10 min. After the addition of TEA, the solution was stirred for an additional 15 min and subsequently transferred to a 1000 ml separatory funnel. The solution was washed with 150 ml of a 1.0 M solution of HCl (1×), 100 ml of 0.1 M solution of NaOH (2×), 100 ml of 1.0 M solution of HCl (1×), and 100 ml of deionized water (3×). The methylene chloride layer was extracted, dried over MgSO4 for 1 hour, and filtered. The methylene chloride was removed in vacuo, and a viscous oil was recovered. The viscous oil was placed into a minimal amount of methylene chloride and crystallized from hexanes after 2-3 weeks time (slow evaporation of solvent occurred during crystallization) to afford a white, crystalline solid. The solid was filtered and dried in vacuo (30 mm Hg) overnight.

Workup

  1. customA 500 ml three-necked round-bottom flask equipped with a magnetic stirrer
  2. customsubsequently transferred to a 1000 ml separatory funnel
  3. washThe solution was washed with 150 ml of a 1.0 M solution of HCl (1×), 100 ml of 0.1 M solution of NaOH (2×), 100 ml of 1.0 M solution of HCl (1×), and 100 ml of deionized water (3×)
  4. extractionThe methylene chloride layer was extracted
  5. dry with materialdried over MgSO4 for 1 hour
  6. filtrationfiltered
  7. customThe methylene chloride was removed in vacuo
  8. customa viscous oil was recovered
  9. customcrystallized from hexanes after 2-3 weeks
  10. customtime (slow evaporation of solvent occurred during crystallization)
  11. customto afford a white, crystalline solid
  12. filtrationThe solid was filtered
  13. customdried in vacuo (30 mm Hg) overnight

Sources & evidence

ORD record
ord-030534b377084e57912edf9db45eb7b3
Source dataset
uspto-grants-2009_03
Patent number
US07511092B2

Reaction notes

Loading…