Phloroglucinol → HCID 5428529, compound

HRID 353486Notes

Reaction equation

HRID 353486 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].OS(C(F)(F)F)(=O)=O>>[OH:2][C:1]1[C:9]2[C:4]([CH2:6][CH3:7])=[CH:3][C:1](=[O:2])[O:8][C:7]=2[CH:6]=[C:4]([OH:5])[CH:3]=1

Participants

3

Reactant 2

HCID 359PhloroglucinolHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 5428529HCID 5428529, compoundYield 127.8%

Procedure

A suspension of phloroglucinol (1.04 g, 8.35 mmol) in ethyl propionyl acetate (1.24 mL, 8.71 mmol) was added over 0.5 h to triflic acid (2 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 white solid (1.1 g, 83.2%): mp. 248-252° C.; 1H NMR (DMSO-d6) δ1.15 (t, 3H), 2.91 (q, 2H), 5.83 (s, 1H), 6.17 (d, 1H), 6.26 (d, 1H) 10.3 (s, 1H) 10.6 (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-7c9c133eef6e433e997e3b98e0c2471f
Source dataset
uspto-grants-2004_06
Patent number
US06753348B2

Reaction notes

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