Water → 2,3-Epoxypropyl 3-methylflavone-8-carboxylate

HRID 464981Notes

Reaction equation

HRID 464981 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:22]1[CH2:26][CH:23]1[CH2:24]O.C(N(CC)CC)C.O>C1C=CC=CC=1>[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([C:13]([O:15][CH2:24][CH:23]3[O:22][CH2:26]3)=[O:14])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11164GlycidolHCID 770163-Methylflavone-8-carboxylic acid

Product 1

HCID 102463862,3-Epoxypropyl 3-methylflavone-8-carboxylateYield 75.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

21.3 g of 3-methylflavone-8-carboxylic acid were slowly added, over a period of 4 hours at 20° C., to a stirred solution of 5.55 g of 2,3-epoxy-1-propanol and 8.34 g of triethylamine in 165 ml of anhydrous benzene. The mixture was permitted to stand at 20°-25° C. for 20 hours, and then 60 ml of water were added. The entire reaction mass was stirred for 15 minutes and the layers were separated. The organic layer was washed and dried, the solvent was evaporated off and 18.95 g of 2,3-epoxypropyl 3-methylflavone-8-carboxylate, m.p. 103°-105° C., were obtained.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed
  3. customdried
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-07777b7bc34747e9855f4006a88dbfee
Source dataset
uspto-grants-1985_10
Patent number
US04550115

Reaction notes

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