Carbon Dioxide → HCID 14204650, compound

HRID 1710154Notes

Reaction equation

HRID 1710154 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:10].[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+].[OH-].[Na+].[C:25](=[O:27])=O>S(=O)(=O)(O)O.C1(C)C(C)=CC=CC=1>[CH3:10][C:9]([C:15]1[CH:16]=[C:11]([C:9]([CH3:10])([CH3:8])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[C:13]([C:17]([OH:18])=[O:20])[C:25]=1[OH:27])([CH3:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 996PhenolHCID 7407Alpha-MethylstyreneHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 14204650HCID 14204650, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7237O-XyleneSolvent2×

Conditions

Temperature
50 °C

Procedure

Charged in a reactor equipped with a thermometer, reflux condenser, dropping funnel and stirrer were 9.4 g of phenol and 0.2 g of sulfuric acid. Then, 23.6 g of α-methylstyrene was added dropwise under stirring at 50° C. over 5 hours from a dropping funnel. After completion of the dropwise addition, the reaction mixture was aged for 5 hours and then poured into a dilute aqueous solution of sodium carbonate. The resultant mixture was separated to obtain an oil layer. The oil layer was then distilled in vacuo. At a vacuum level of 3-4 mmHg, 22 g of a fraction having a boiling point of at least 220° C. was obtained. Thereafter, 7.5 g of a 40% aqueous solution of caustic soda was added to the fraction, followed by dehydration under reflux of xylene. After the dehydration, the xylene mixture was transferred to an autoclave and carbon dioxide was then charged to 30 kg/cm2 at 160° C. The contents were then reacted for 5 hours at the same temperature. After the reaction, the autoclave was cooled, the remaining gas was purged, the reaction mixture was extracted with hot water and the extract was neutralized with dilute sulfuric acid. As a result, crystals were caused to precipitate. Those crystals were then collected by filtration, followed by recrystallization using an aqueous acetic acid solution to obtain 8 g of 3,5-di(α,α-dimethylbenzyl)salicylic acid. A zinc salt was produced from the salicylic acid compound in the same manner as in Example 2.

Workup

  1. additionCharged in a reactor
  2. customequipped with a thermometer
  3. temperaturereflux condenser
  4. additionAfter completion of the dropwise addition
  5. waitthe reaction mixture was aged for 5 hours
  6. customThe resultant mixture was separated
  7. customto obtain an oil layer
  8. distillationThe oil layer was then distilled in vacuo
  9. customwas obtained
  10. additionwas then charged to 30 kg/cm2 at 160° C
  11. customThe contents were then reacted for 5 hours at the same temperature
  12. customAfter the reaction
  13. temperaturethe autoclave was cooled
  14. customthe remaining gas was purged
  15. extractionthe reaction mixture was extracted with hot water
  16. customto precipitate
  17. filtrationThose crystals were then collected by filtration
  18. customfollowed by recrystallization

Sources & evidence

ORD record
ord-0a79a28d82b14608866143c4a8fff112
Source dataset
uspto-grants-1990_08
Patent number
US04952648

Reaction notes

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