Acetic Acid → HCID 20318402, compound

HRID 1287340Notes

Reaction equation

HRID 1287340 reaction equation
[Na].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[C:7]=1[OH:14])([CH3:5])([CH3:4])[CH3:3].[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17].C(O)(=O)C>C1(C)C=CC=CC=1>[C:2]([C:6]1[C:7]([OH:14])=[C:8]([CH3:13])[C:9]([CH3:12])=[C:10]([CH2:17][CH2:16][C:15]([O:19][CH3:20])=[O:18])[CH:11]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 170766Phenol, 6-(1,1-dimethylethyl)-2,3-dimethyl-HCID 5360545Sodium2×

Product 1

HCID 20318402HCID 20318402, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.53 grams of sodium metal was added in small pieces to 240.6 grams of 2-tert.-butyl-5,6-dimethylphenol warmed at 60°. The reaction mixture was then heated at 120° with stirring for 2 hours, during which time the sodium metal was completely reacted. 174 grams of methyl acrylate was then added gradually over a period of 1 hour so that the temperature was maintained at 120°. The reaction mixture was then heated at 120° to 130° for an additional 4 hours. 3.9 ml. of acetic acid was then added. The reaction mixture was diluted with 600 ml. of toluene and warmed to dissolve a precipitate. The toluene solution was washed successively with 2N sodium carbonate, saturated sodium chloride, water, dilute aqueous hydrochloric acid and finally with water until the water washings were almost neutral. After drying over sodium sulfate, the clear toluene solution was evaporated at 20 mm Hg. pressure and finally at 1 mm. Hg. pressure for 2 hours. The crude residual product was crystallized from a mixture of 450 ml. of isopropanol and 200 ml. water and kept at about 15°C overnight. The thick crystalline slurry was filtered, the filter cake being washed with a little cold isopropanol-water mixture. After drying and recrystallization, the desired product was obtained as white crystals melting at 74° to 76°C (Compound 1).

Workup

  1. temperaturewarmed at 60°
  2. temperatureThe reaction mixture was then heated at 120°
  3. customwas completely reacted
  4. temperaturewas maintained at 120°
  5. temperatureThe reaction mixture was then heated at 120° to 130° for an additional 4 hours
  6. additionThe reaction mixture was diluted with 600 ml
  7. dissolutionto dissolve a precipitate
  8. washThe toluene solution was washed successively with 2N sodium carbonate, saturated sodium chloride, water, dilute aqueous hydrochloric acid and finally with water until the water washings
  9. dry with materialAfter drying over sodium sulfate
  10. customthe clear toluene solution was evaporated at 20 mm Hg
  11. customThe crude residual product was crystallized from a mixture of 450 ml
  12. waitwater and kept at about 15°C overnight
  13. filtrationThe thick crystalline slurry was filtered
  14. washthe filter cake being washed with a little cold isopropanol-water mixture
  15. customAfter drying
  16. customrecrystallization

Sources & evidence

ORD record
ord-ad82eea701704f26a0ea57af76674bc5
Source dataset
uspto-grants-1976_10
Patent number
US03984460

Reaction notes

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