N-(hydroxymethyl)phthalimide → HCID 15895365, compound

HRID 1954672Notes

Reaction equation

HRID 1954672 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]1[O:17][C:16]2[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:15]=2[O:14]1.O[CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>C(Cl)(Cl)Cl.ClCCl>[OH:22][C:19]1[CH:18]=[C:16]2[O:17][CH2:13][O:14][C:15]2=[CH:21][C:20]=1[CH2:24][N:25]1[C:26](=[O:35])[C:27]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:28]2[C:29]1=[O:30]

Participants

6

Reactant 3

HCID 8354N-(hydroxymethyl)phthalimideHCID 68289SesamolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15895365HCID 15895365, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (3.61 g, 19.0 mmol) was dried by azeotropic distillation in a chloroform solution (100 mL). The remaining solution (50 mL) was cooled, 9.14 g (66.2 mmol) sesamol, 10.01 g (57 mmol) N--(hydroxymethyl)-phthalimide, and 100 mL chloroform were added, and the resulting green solution was refluxed overnight. The black reaction mixture was cooled to ambient, diluted to 500 mL with chloroform, and washed three times with saturated sodium bicarbonate. The pooled aqueous phases were back extracted with ethyl acetate, which was combined with the chloroform solution and dried over sodium sulfate. The residue that resulted from evaporation of solvents on a rotary evaporator was taken up in dichloromethane and filtered through a short column of silica gel. A dichloromethane rinse of the silica gel was combined with the eluent and evaporated to yield 9.3 g of N--(2-hydroxy-4,5-methylenedioxybenzyl)-phthalimide as a yellow solid (55%), which exhibited one spot on TLC (Rf =0.6; dichloro-methane). IR: 1768 and 1699 cm-1. 1HNMR (200 MHz): δ 7.81-7.90 (2H, m); 7.70-7.79 (2H, m); 7.76 (1H, s); 6.86 (1H, s); 6.52 (1H, s); 5.88 (2H, s); and 4.73 ppm (2H, s).

Workup

  1. temperaturethe resulting green solution was refluxed overnight
  2. customThe black reaction mixture
  3. temperaturewas cooled to ambient,
  4. washwashed three times with saturated sodium bicarbonate
  5. extractionThe pooled aqueous phases were back extracted with ethyl acetate, which
  6. dry with materialdried over sodium sulfate
  7. customThe residue that resulted from evaporation of solvents on a rotary evaporator
  8. filtrationfiltered through a short column of silica gel
  9. washA dichloromethane rinse of the silica gel
  10. customevaporated

Sources & evidence

ORD record
ord-b6b644c515134654baa4f3fff63fa897
Source dataset
uspto-grants-2000_09
Patent number
US06124278

Reaction notes

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