Phloroglucinol → 2H-1-Benzopyran-2-one, 5,7-dihydroxy-4-phenyl-

HRID 840326Notes

Reaction equation

HRID 840326 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CC[O:12][C:13]([CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)=O.OS(C(F)(F)F)(=O)=O>>[OH:2][C:1]1[C:9]2[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:13](=[O:12])[O:8][C:7]=2[CH:6]=[C:4]([OH:5])[CH:3]=1

Participants

4

Reactant 3

HCID 359PhloroglucinolHCID 7170Ethyl benzoylacetateHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 53986492H-1-Benzopyran-2-one, 5,7-dihydroxy-4-phenyl-Yield 74.8%

Procedure

A suspension of phloroglucinol (2.10 g, 12.9 mmol) in ethyl benzoyl acetate (2.41 mL, 13.8 mmol) was added over 0.5 hours to triflic acid (4 mL). The reaction was mechanically stirred in an ice bath for 16 h The reaction was quenched by carefully pouring into an ice bath. The solid was filtered and dried yielding a yellow solid (2.43 g, 74.8%): mp. 179-182° C.; 1H NMR (DMSO-d6) δ 5.75 (s, 1H), 6.15 (s, 1H), 6.25 (s, 1H).

Workup

  1. customwas quenched
  2. additionby carefully pouring into an ice bath
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-d999e4311faa43d5baebd4e243875178
Source dataset
uspto-grants-2002_04
Patent number
US06365626B1

Reaction notes

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