Acetic Acid → HCID 3319467, compound

HRID 1157477Notes

Reaction equation

HRID 1157477 reaction equation
F[B-](F)(F)F.[C:6]1([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[C:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O+:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:30]1(=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][C:31]1=[O:36].C(O)(=O)C.C(N(CC)CC)C>CO>[CH2:17]([C:16]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[C:14]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:32]2[CH2:33][CH2:34][CH2:35][C:30](=[O:37])[C:31]=2[O:36]1)[C:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 130061,2-CyclohexanedioneHCID 9930615Pyrylium, 2,4,6-triphenyl-, tetrafluoroborate(1-)

Product 1

HCID 3319467HCID 3319467, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 13.51 g of 2,4,6-triphenylpyryliumtetrafluoroborate (34.1 mmol) and 4.78 g of cyclohexane-1,2-dione (42.6 mmol) is heated to boiling point in methanol, then a solution of 4.56 g of acetic acid (75.9 mmol) and 7.68 g of triethylamine (75.9 mmol) in a little methanol is added dropwise. After heating at reflux for 7 h, the solution is allowed to cool to room temperature. A light yellow precipitate is extracted by suction, washed in portions with 100 ml of ice-cold methanol and dried to constant weight. 11.37 g of a light yellow powder (79.3%) with a melting point of 178-179° C. (lit.: 182-184° C.) is obtained.

Workup

  1. temperatureis heated
  2. temperatureAfter heating
  3. temperatureat reflux for 7 h
  4. extractionA light yellow precipitate is extracted by suction
  5. washwashed in portions with 100 ml of ice-cold methanol
  6. customdried to constant weight

Sources & evidence

ORD record
ord-7830f76f117a413b8d9c7cedb356d4ab
Source dataset
uspto-grants-2010_10
Patent number
US07807687B2

Reaction notes

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