Benzaldehyde → 4-Methyl-2-phenyltetrahydro-2H-pyran

HRID 1587663Notes

Reaction equation

HRID 1587663 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][O:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1.C=C1CCOC(C2C=CC=CC=2)C1.C(=O)C1C=CC=CC=1.CC(CCO)=C>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][O:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 129883-Methyl-3-buten-1-olHCID 1084425,6-dihydro-4-methyl-2-phenyl-2H-pyranHCID 1084442H-Pyran, tetrahydro-4-methylene-2-phenyl-

Product 1

HCID 30240034-Methyl-2-phenyltetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In an autoclave, 10 g of a mixture of 5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylene-2-phenyl-2H-pyran (prepared from benzaldehyde and isoprenol as described in Swiss Pat. No. 655 932) in 50 ml of ethyl alcohol were hydrogenated in the presence of 0.1 g of 10% Pd on charcoal to yield 9.7 g of pure tetrahydro-4-methyl-2-phenyl-2H-pyran.

Sources & evidence

ORD record
ord-e4fa6bb9f1434516bfd1388bd35344be
Source dataset
uspto-grants-1993_06
Patent number
US05219836

Reaction notes

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