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

HRID 1275252Notes

Reaction equation

HRID 1275252 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) δ5.75 (s, 1H), 6.15 (s, 1H), 6.25 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-397aaabfb7af49a0ae5a893b9497bdbf
Source dataset
uspto-grants-2000_12
Patent number
US06160010

Reaction notes

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