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

HRID 1953169Notes

Reaction equation

HRID 1953169 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]=[CH:10][C:11](=[CH2:13])[CH3:12].O>CCCCCC>[CH3:12][C:11]1[CH2:13][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH2:9][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 6557Isoprene

Product 1

HCID 1084432H-Pyran, 3,6-dihydro-4-methyl-2-phenyl-Yield 42%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Bis-trifluoromethanesulphonimide (70, 5 mg, 0.25 mmol) was stirred in hexane (4 ml) at room temperature. Benzaldehyde (510 μl, 5.0 mmol) and isoprene (750 μl, 7.5 mmol) were added and the mixture stirred at room temperature overnight. Water (5 ml) was added and the aqueous layer was extracted with hexane (3×3 ml). The combined organic layers were filtered through celite and analysed by glc. A yield of 42% of 4-methyl-6-phenyl-5,6-dihydropyran was observed.

Workup

  1. extractionthe aqueous layer was extracted with hexane (3×3 ml)
  2. filtrationThe combined organic layers were filtered through celite and analysed by glc

Sources & evidence

ORD record
ord-49cccaa4e166418c877cfdcfdd9981ba
Source dataset
uspto-grants-2000_09
Patent number
US06114548

Reaction notes

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