Phloroglucinol → HCID 5428529, compound

HRID 840324Notes

Reaction equation

HRID 840324 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 in to 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 in to an ice bath
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-8803afeda6e041528bfe200cadd8bdd8
Source dataset
uspto-grants-2002_04
Patent number
US06365626B1

Reaction notes

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