Benzaldehyde → 2H-Pyran, 3,6-dihydro-4-methyl-2-phenyl-

HRID 1953168Notes

Reaction equation

HRID 1953168 reaction equation
OS(C(F)(F)F)(=O)=O.[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:17]=[CH:18][C:19](=[CH2:21])[CH3:20]>C1(C)C=CC=CC=1>[CH3:20][C:19]1[CH2:21][CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:16][CH2:17][CH:18]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6557IsopreneHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 1084432H-Pyran, 3,6-dihydro-4-methyl-2-phenyl-Yield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a rapidly stirred solution of 70% aqueous triflic acid (2.10 g, 0.01 mol) and benzaldehyde (106.1 g, 1.0 mol) in 100 ml toluene was added isoprene (150 cm3, 1.5 mol) over 4 hrs. at 25° C. The mixture was stirred at room temperature for a further 11 hours after which the reaction mixture was quenched by the addition of Polyrad* (2 g) and solid sodium carbonate (5 g). The crude mixture was distilled under reduced pressure to give pure rosyrane (56% yield) as a colorless oil.

Workup

  1. customat 25° C
  2. customwas quenched by the addition of Polyrad* (2 g) and solid sodium carbonate (5 g)
  3. distillationThe crude mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-a6574ec596c247e9b29b25e52430ba01
Source dataset
uspto-grants-2000_09
Patent number
US06114548

Reaction notes

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