Acetic Acid → HCID 22274543, compound

HRID 494792Notes

Reaction equation

HRID 494792 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.[BrH:9].C(O)(=[O:12])C.[C:14]([CH:17]1[CH2:22][CH2:21]O[C:18]1=[O:19])(=O)[CH3:15]>O>[Br:9][CH2:21][CH2:22][C:17]1[C:18](=[O:19])[O:5][C:4]2[C:6]([C:14]=1[CH3:15])=[CH:7][C:8]([OH:12])=[CH:1][CH:3]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 5054ResorcinolHCID 106012-Acetylbutyrolactone

Product 1

HCID 22274543HCID 22274543, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of resorcinol (7.03 g, 64.0 mmol) in a solution consisting of HBr (104 mL, 422 mmol) and glacial acetic acid (10 mL) at 0° C. was slowly added 2-acetylbutyrolactone (5.8 mL, 54 mmol). The mixture was warmed to ambient temperature and then heated to reflux for 2 hours. The mixture was cooled to ambient temperature and diluted with water (350 mL). The mixture was filtered and the solid dried in vacuo overnight to give the titled compound (15.5 g, 85%). 1H NMR (300 MHz, CD3OD) δ 10.5 (s, 1H), 7.6 (d, J=8.7 Hz, 1H), 6.8 (dd, J=6.6 Hz, 11.4 Hz, 1H), 6.7 (d, J=2.1 Hz, 1H), 3.6 (t, J=7.5 Hz, 2H), 3.1 (t, J=7.6 Hz, 2H), 2.4 (s, 3H); MS (DCI) m/z 283, 284 (M+H)+;

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. filtrationThe mixture was filtered
  5. customthe solid dried in vacuo overnight

Sources & evidence

ORD record
ord-c99bb977600542ee8108813d7db1a64e
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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