Methyl (3-methyl-1-butenyl) ether → 2-(2-Formyl-3-methylbutyl)-3-isopropenyl-1-methyl-1-cyclopentene

HRID 437489Notes

Reaction equation

HRID 437489 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:10])(O)[C:5]1=[CH2:11])([CH3:3])=[CH2:2].[CH3:12][CH:13]([CH3:18])[CH:14]=[CH:15][O:16]C>P(=O)(O)(O)O>[CH:15]([CH:14]([CH:13]([CH3:18])[CH3:12])[CH2:11][C:5]1[CH:4]([C:1]([CH3:3])=[CH2:2])[CH2:8][CH2:7][C:6]=1[CH3:10])=[O:16]

Participants

4

Reactant 2

HCID 141672Methyl (3-methyl-1-butenyl) etherHCID 30164943-Isopropenyl-1-methyl-2-methylenecyclopentan-1-ol

Product 1

HCID 213885282-(2-Formyl-3-methylbutyl)-3-isopropenyl-1-methyl-1-cyclopenteneYield 45%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

According to the procedure described in Example 7, by the reaction of 30.4 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol with 50 g of methyl (3-methyl-1-butenyl) ether in the presence of 7 drops of 85% phosphoric acid there was obtained 2-(2-formyl-3-methylbutyl)-3-isopropenyl-1-methyl-cyclopent-1-ene in 45% yield; boiling point 0.005 = 55°-56° C; nD20 = 1.4808; IRfilm :νmax = 3080, 2725, 1725, 1642, 1460/40, 1390/70 and 890 cm-1. The compound has a cedar-like, woody, remotely floral fragrance.

Sources & evidence

ORD record
ord-31708d8ff0f1478cbfb87d9d4c2eb329
Source dataset
uspto-grants-1977_06
Patent number
US04031132

Reaction notes

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