Dimethylformamide → HCID 19595924, compound

HRID 612792Notes

Reaction equation

HRID 612792 reaction equation
[OH:1][C:2]1[C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]([OH:18])=O)[CH:8]=2)[CH:3]=1.S(Cl)(Cl)=O.CN(C)[CH:25]=[O:26]>O1CCCC1>[OH:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]([O:26][CH2:25][CH2:10][CH2:11][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:18])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 12067409HCID 12067409, compound

Product 1

HCID 19595924HCID 19595924, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In 10.0 g of tetrahyrofuran, 1.00 g of 2-hydroxy-6-hydroxycarbonyl-3-methoxycarbonylnaphthalene is suspended. To this, 0.94 g of thionyl chloride and a small amount of N,N-dimethylformamide are added, and heated to 50° C. After allowing to proceed the reaction for about 3 hours, the solvent and other volatile are evaporated. To the residue, a solution of 1.27 g of n-decanol dissolved in 10.0 g of tetrahydrofuran is added, and reacted for about 20 hours under reflux. After evaporating the solvent, 15.0 g of N,N-dimethylformamide, 15.0 g of methanol, and 180.0 g of 5% aqueous sodium hydrogencarbonate are added, and reacted for 20 hours at 60° C. After removing insoluble matter, the pH of the reaction mixture is adjusted to pH 2 at 50° C., and the precipitate is recovered by filtration. The product was washed with warm water and methanol, and dried to yield 1.33 g of 2-hydroxy-3-hydroxycarbonyl-6-decyloxycarbonylnaphthalene as a white-yellow powder (melting/decomposing point: 269.2° C. (dec.)).

Workup

  1. customthe reaction for about 3 hours
  2. customthe solvent and other volatile are evaporated
  3. dissolutionTo the residue, a solution of 1.27 g of n-decanol dissolved in 10.0 g of tetrahydrofuran
  4. additionis added
  5. customreacted for about 20 hours
  6. temperatureunder reflux
  7. customAfter evaporating the solvent, 15.0 g of N,N-dimethylformamide, 15.0 g of methanol, and 180.0 g of 5% aqueous sodium hydrogencarbonate
  8. additionare added
  9. customreacted for 20 hours at 60° C
  10. customAfter removing insoluble matter
  11. customis adjusted to pH 2 at 50° C.
  12. filtrationthe precipitate is recovered by filtration
  13. washThe product was washed with warm water and methanol
  14. customdried

Sources & evidence

ORD record
ord-c147e64011f74bd1b94e25455f5f8ada
Source dataset
uspto-grants-1999_12
Patent number
US06005085

Reaction notes

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