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

HRID 353488Notes

Reaction equation

HRID 353488 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-1ed4f05d102b49fe865f312cfe1c9b9d
Source dataset
uspto-grants-2004_06
Patent number
US06753348B2

Reaction notes

Loading…