Carbon Dioxide → HCID 23459854, compound

HRID 2287213Notes

Reaction equation

HRID 2287213 reaction equation
[CH3:1][C:2]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C:4]([CH3:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5].[C:26](=O)([O-:28])[O-:27].[K+].[K+].C(=O)=O.O>C1C=CC=CC=1>[CH3:1][C:2]([C:19]1[CH:24]=[C:23]([C:26]([OH:28])=[O:27])[C:22]([OH:25])=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:3][C:4]([CH3:5])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:12]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 11430Potassium CarbonateHCID 607459HCID 607459, compound

Product 1

HCID 23459854HCID 23459854, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
180 °C

Procedure

33.0 g (0.1 mole) of p-(1,3-dimethyl-1,3-diphenylbutyl)phenol and 100 g of anhydrous potassium carbonate were placed in an autoclave and thereto, carbon dioxide gas was introduced at a pressure of 40 Kg/cm2. Then, the mixture was shaken at 180° C. for 5 hours. After cooling to room temperature, the pressure in the autoclave was returned to atmospheric pressure and then, 200 ml of water and 400 ml of benzene were added to the reaction product in the autoclave, followed by heating them in order to dissolve the reaction product in these solvents. The organic phase separated out was taken out of the autoclave and shaken with a dilute hydrochloric acid solution to convert the potassium salt into the corresponding free acid. Then, it was washed with water, dried and then, concentrated in order to remove the benzene. Thus, white needle crystal was separated out. The crystal was filtered off to obtain 31.8 g of 5-(1,3-dimethyl-1,3-diphenylbutyl)salicylic acid (yield: 85%, mp: 153°-155° C.).

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureby heating them in order
  3. dissolutionto dissolve the reaction product in these solvents
  4. customThe organic phase separated out
  5. stirringshaken with a dilute hydrochloric acid solution
  6. washThen, it was washed with water
  7. customdried
  8. concentrationconcentrated in order
  9. customto remove the benzene
  10. customThus, white needle crystal was separated out
  11. filtrationThe crystal was filtered off

Sources & evidence

ORD record
ord-1b41e96ebdab4303b3701a6b7a2a3a5b
Source dataset
uspto-grants-1981_05
Patent number
US04269893

Reaction notes

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