Phloroglucinol → HCID 5428529, compound

HRID 325016Notes

Reaction equation

HRID 325016 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) δ 1.15 (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-1225ee4867b3427ab098778a692a9328
Source dataset
uspto-grants-2001_04
Patent number
US06221900B1

Reaction notes

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