Phloroglucinol → HCID 5428529, compound

HRID 380649Notes

Reaction equation

HRID 380649 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-7801f79f033044ba86811eebc219cc49
Source dataset
uspto-grants-2001_10
Patent number
US06303652B1

Reaction notes

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