Dimethylformamide → HCID 11369034, compound

HRID 1532419Notes

Reaction equation

HRID 1532419 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8](=[O:12])[O:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanolHCID 5281426Umbelliferone

Product 1

HCID 11369034HCID 11369034, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4.87 g (30 mmol) of 7-hydroxy-coumarin, 6.17 g (45.2 mmol) of 6-chlorohexanol and 6.56 g (47.5 mmol) of potassium carbonate were treated with 50 ml of absolute N,N-dimethylformamide and stirred at 100° C. overnight. Subsequently, the batch was poured into water. The white precipitate which separated was filtered off and rinsed with water. The mother liquor was evaporated to dryness in a vacuum, taken up in a small amount of water and extracted several times with ethyl acetate. The precipitate and the ethyl acetate phases were combined, dried over sodium sulphate, evaporated and, for purification, chromatographed on silica gel with an eluent mixture of ethyl acetate and cyclohexane in the ratio 1:1. Therefrom there resulted 7 g of 7-(6-hydroxy-hexyloxy)-2H-1-benzopyran-2-one as white crystals.

Workup

  1. customThe white precipitate which separated
  2. filtrationwas filtered off
  3. washrinsed with water
  4. customThe mother liquor was evaporated to dryness in a vacuum
  5. extractionextracted several times with ethyl acetate
  6. dry with materialdried over sodium sulphate
  7. customevaporated and, for purification
  8. customchromatographed on silica gel with an eluent mixture of ethyl acetate and cyclohexane in the ratio 1:1

Sources & evidence

ORD record
ord-f8f0b093aedf491ca24f785597bbee60
Source dataset
uspto-grants-2001_03
Patent number
US06201087B1

Reaction notes

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