Water → HCID 86680884, compound

HRID 1052941Notes

Reaction equation

HRID 1052941 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:30])[C:26](=[O:29])[CH:27]=[CH2:28].C(=O)([O-])[O-:32].[K+].[K+].O>CN(C)C=O.C(O)C.CC(C)=O>[C:26]([N:25]([CH3:30])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[C:4]([C:9]([OH:8])=[O:10])[C:5](=[CH:11][CH:12]=1)[C:6]([OH:32])=[O:7])(=[O:29])[CH:27]=[CH2:28]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6397475-Hydroxy-1,3-dihydro-2-benzofuran-1,3-dioneHCID 86680883HCID 86680883, compound

Product 1

HCID 86680884HCID 86680884, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-hydroxyphthalic anhydride (6.70 g; 40.8 mmol), BHT (10 mg) and N-(11-bromoundecyl)-N-methyl acrylamide (13.00 g; 40.8 mmol) were dissolved in N,N-dimethylformamide (100 ml). Potassium carbonate (5.64 g; 40.8 mmol) was added. The yellow suspension was stirred at RT. Water (200 ml) was added to the reaction mixture after 20 d and the whole stirred for 1 h at RT. An oily white solid precipitated from the initially cloudy solution. The solvent was decanted off. The residue was dissolved in dilute aqueous Na2CO3 solution (5%; 100 ml). The milky/cloudy aqueous phase was washed with MtBE (5×100 ml). Diluted hydrochloric acid (2N, 100 ml) was added to the water phase (pH=1) and extraction with MtBE (8×100 ml) took place. The combined extracts were dried over Na2SO4, filtered and concentrated on the rotary evaporator. Chloroform (150 ml) was added to the residue and the whole stirred at RT. After 20 h the suspension was filtered. The filtration residue was washed with chloroform (50 ml) and discarded. The filtrate was concentrated on the rotary evaporator. The residue was dissolved in chloroform (50 ml). Acetonitrile (50 ml) was added. After 72 h storage at −18° C. the solvent was decanted off and the residue dried under a fine vacuum. 3.84 g (9.2 mmol; 22% yield) of a white solid was obtained (melting point: 95° C.), which dissolves very well e.g. in ethanol or acetone.

Workup

  1. stirringthe whole stirred for 1 h at RT
  2. customAn oily white solid precipitated from the initially cloudy solution
  3. customThe solvent was decanted off
  4. dissolutionThe residue was dissolved in dilute aqueous Na2CO3 solution (5%; 100 ml)
  5. washThe milky/cloudy aqueous phase was washed with MtBE (5×100 ml)
  6. additionDiluted hydrochloric acid (2N, 100 ml) was added to the water phase (pH=1) and extraction with MtBE (8×100 ml)
  7. dry with materialThe combined extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on the rotary evaporator
  10. additionChloroform (150 ml) was added to the residue
  11. stirringthe whole stirred at RT
  12. filtrationAfter 20 h the suspension was filtered
  13. washThe filtration residue was washed with chloroform (50 ml)
  14. concentrationThe filtrate was concentrated on the rotary evaporator
  15. dissolutionThe residue was dissolved in chloroform (50 ml)
  16. additionAcetonitrile (50 ml) was added
  17. customAfter 72 h storage at −18° C. the solvent was decanted off
  18. customthe residue dried under a fine vacuum
  19. custom3.84 g (9.2 mmol; 22% yield) of a white solid was obtained (melting point: 95° C.), which

Sources & evidence

ORD record
ord-30371194de5d421eb0f539287acda143
Source dataset
uspto-grants-2016_07
Patent number
US09393181B2

Reaction notes

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