O-Cresol → 6-Cyclopentyl-o-cresol

HRID 1886553Notes

Reaction equation

HRID 1886553 reaction equation
B(F)(F)F.P(=O)(O)(O)O.[C:10]1([CH3:17])[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:18]1[CH2:22][CH2:21][CH2:20][CH:19]=1>CCCCC>[CH:18]1([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:17])[C:15]=2[OH:16])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 335O-CresolHCID 8882CyclopenteneHCID 11480637Phosphoric acid;trifluoroborane

Product 1

HCID 741356-Cyclopentyl-o-cresolYield 37%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

170 ml of boron trifluoride/phosphoric acid adduct are added to 1.08 kg (10 moles) of o-cresol in 400 ml of pentane. 680 g (10 moles) of cyclopentene, dissolved in 1 l of pentane, are added dropwise at the reflux temperature in the course of 3 hours. The mixture is stirred for a further hour at the reflux temperature and then poured into ice water. The organic phase is separated off and is extracted with 4 times 600 ml of 10% strength sodium hydroxide solution. The organic phase is dried and evaporated down and the residue is distilled (84°-88° C./0.2 mbar). 515 g of 2-cyclopentyl-6-methylphenol (corresponding to 37% of theory, based on converted cresol) are obtained. 217 g of o-cresol and 282 g of 4-cyclopentyl-2-methylphenol are obtained from the alkaline wash solution after acidification, extraction and distillation.

Workup

  1. additionare added dropwise at the reflux temperature in the course of 3 hours
  2. customThe organic phase is separated off
  3. extractionis extracted with 4 times 600 ml of 10% strength sodium hydroxide solution
  4. customThe organic phase is dried
  5. customevaporated down
  6. distillationthe residue is distilled (84°-88° C./0.2 mbar)

Sources & evidence

ORD record
ord-d6f8ade9c273452981fc17fc1568dd55
Source dataset
uspto-grants-1992_09
Patent number
US05151548

Reaction notes

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