Triethylamine → 2-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate

HRID 1532416Notes

Reaction equation

HRID 1532416 reaction equation
[CH3:1][C:2](=[CH2:22])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)=[O:4].S(Cl)(Cl)=O.O[C:28]1[CH:37]=[C:36]2[C:31]([CH:32]=[CH:33][C:34](=[O:38])[O:35]2)=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C=O)C.C1COCC1>[CH3:22][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:28]2[CH:29]=[CH:30][C:31]3[CH:32]=[CH:33][C:34](=[O:38])[O:35][C:36]=3[CH:37]=2)=[O:18])=[CH:20][CH:21]=1)=[O:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 37303444-{[6-(Methacryloyloxy)hexyl]oxy}benzenecarboxylic acidHCID 5281426Umbelliferone

Product 1

HCID 212518122-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoateYield 59.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8.5 g (0.028 mol) of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoic acid were treated with 10 ml of thionyl chloride and 3 drops of DMF and boiled under reflux for 4 hours. The excess thionyl chloride was removed completely, firstly in a water-jet vacuum and subsequently in a high vacuum. The acid chloride remaining was taken up in 20 ml of THF and slowly added dropwise at 0° C. to a suspension of 4.09 g (0.025 mol) of 7-hydroxy-coumarin and 4.25 ml of triethylamine in 30 ml of THF. The batch was stirred at room temperature overnight, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography and subsequently by recrystallization from ethanol. 6.71 g of 2-oxo-2H-1-benzopyran-7-yl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were isolated as a white powder; m.p. 98-104.5° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe excess thionyl chloride was removed completely, firstly in a water-jet vacuum and subsequently in a high vacuum
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by column chromatography and subsequently by recrystallization from ethanol

Sources & evidence

ORD record
ord-0e78fb21530f41a2b50f3c1a6561bd49
Source dataset
uspto-grants-2001_03
Patent number
US06201087B1

Reaction notes

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