Phosphoric Acid → HCID 12715053, compound

HRID 2269587Notes

Reaction equation

HRID 2269587 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=CC=1.P(=O)(O)(O)O.C1CC=CC=1>C(C(C)=O)C(C)C.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]=[CH:16]2)[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 1140Toluene2×HCID 7612CyclopentadieneHCID 113352,6-Dimethylphenol

Product 1

HCID 12715053HCID 12715053, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 2-liter flask having a stirrer, a condenser and a thermometer, 366 g of 2,6-dimethylphenol, 360 g of toluene and 102 g of phosphoric acid were introduced, and a solution of mixture of 247 g of cyclopentadiene and 200 g of toluene was added dropwise over a period of 3 hours while stirring the mixture under ice cooling, followed by further stirring for 4 hours at room temperature. To the reaction solution thus obtained, tetrahydrofuran (hereinafter “THF”) and methyl isobutyl ketone (hereinafter “MIBK”) were added, and the resultant solution was washed with water until it turned neutral, followed by distillation under reduced pressure. After the reaction solvent had evaporated, unreacted 2,6-dimethylphenol evaporated. A fraction at 3 mmHg and 140° C. was 2,6-dimethyl-4-(2-cyclopenten-1-yl)phenol. The results of analysis by GPC thereof are shown in FIG. 1. Its yield determined by GPC was 94% (area ratio).

Workup

  1. customInto a 2-liter flask having
  2. additionwas added dropwise over a period of 3 hours
  3. stirringby further stirring for 4 hours at room temperature
  4. customTo the reaction solution thus obtained
  5. washthe resultant solution was washed with water until it
  6. distillationfollowed by distillation under reduced pressure
  7. customAfter the reaction solvent had evaporated
  8. customunreacted 2,6-dimethylphenol evaporated
  9. customat 3 mmHg and 140° C.
  10. customThe results of analysis by GPC
  11. customIts yield

Sources & evidence

ORD record
ord-3af76bcebf5548928505196d61a11dba
Source dataset
uspto-grants-2001_12
Patent number
US06329492B1

Reaction notes

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