Potassium Carbonate → HCID 57909153, compound

HRID 1918434Notes

Reaction equation

HRID 1918434 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)[C:3]=1[C:16]([OH:18])=O.C([O-])([O-])=O.[K+].[K+]>S(=O)(=O)(O)O>[CH3:14][C:12]1[C:13]2[C:16](=[O:18])[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:8]=2[CH:9]=[C:10]([CH3:15])[CH:11]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 532252823,3',5'-Trimethyl[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 57909153HCID 57909153, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 ml 1-necked round bottom flask the biphenyl-carboxylic acid 52 (3.0 g, 12.9 mmol) was treated with concentrated sulphuric acid (40 ml) at 0° C. (ice bath). The resulting dark brown solution was stirred for 15 min at 0° C., then for additional 1 h at ambient temperature. The reaction mixture was poured in ice (100 g) whereupon the color changes to a bright yellow. The suspension was neutralized with K2CO3 and extracted with Et2O (3×100 ml). The combined organic phases were washed with brine (75 ml), dried over MgSO4, filtered and the volatiles removed in vacuo to afford 53 (2.8 g, 98%) as yellow crystals. Rf 0.52 (cyclohexane:ethylacetate 10:1). The product was used without any further purification.

Workup

  1. waitfor additional 1 h at ambient temperature
  2. extractionextracted with Et2O (3×100 ml)
  3. washThe combined organic phases were washed with brine (75 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-b021fec436f3400bb8e4ca1c5c30ef20
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

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