Toluene → HCID 22737553, compound

HRID 2269588Notes

Reaction equation

HRID 2269588 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:21][C:22]1[CH:27]=[C:26]([CH:28]2[CH2:32][CH2:31][CH:30]=[CH:29]2)[CH:25]=[C:24]([CH3:33])[C:23]=1[OH:34].C1(C)C=CC=CC=1>CC(CC(C)=O)C.C1COCC1>[OH:9][C:3]1[C:4]([CH3:8])=[CH:5][C:6]([CH:31]2[CH2:30][CH2:29][CH:28]([C:26]3[CH:25]=[C:24]([CH3:33])[C:23]([OH:34])=[C:22]([CH3:21])[CH:27]=3)[CH2:32]2)=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 113352,6-DimethylphenolHCID 12715053HCID 12715053, compound

Product 1

HCID 22737553HCID 22737553, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 2-liter flask having a stirrer, a condenser and a thermometer, 286 g of 2,6-dimethylphenol and 40 g of p-toluenesulfonic acid (hereinafter “PTS”) were introduced, and a solution of mixture of 106 g of 2,6-dimethyl-4-(2-cyclopenten-1-yl)phenol and 106 g of toluene was added dropwise over a period of 1 hour while stirring the mixture kept at 100° C., followed by further stirring for 4 hours at 80° C. To the reaction solution thus obtained, THF and MIBK were added, and the resultant solution was washed with water until it turned neutral, followed by removal of the solvent and 2,6-dimethylphenol using an evaporator.

Workup

  1. customInto a 2-liter flask having
  2. additionwas added dropwise over a period of 1 hour
  3. customkept at 100° C.
  4. stirringby further stirring for 4 hours at 80° C
  5. customTo the reaction solution thus obtained
  6. washthe resultant solution was washed with water until it
  7. customfollowed by removal of the solvent and 2,6-dimethylphenol using
  8. customan evaporator

Sources & evidence

ORD record
ord-facde5d698b44e98896be084dadcb350
Source dataset
uspto-grants-2001_12
Patent number
US06329492B1

Reaction notes

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