cis-2,6,6-Trimethyl-1-[1-hydroxy-2-butenyl]2-cyclohexene → (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

HRID 1448874Notes

Reaction equation

HRID 1448874 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH:10]([OH:14])/[CH:11]=[CH:12]\[CH3:13].CC1C(C(O)/C=C\C)C(C)(C)CCC=1>>[CH3:1][C:2]1[CH:3]([C:10](=[O:14])/[CH:11]=[CH:12]/[CH3:13])[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH:7]=1

Participants

3

Reactant 2

HCID 14355052cis-2,6,6-Trimethyl-1-[1-hydroxy-2-butenyl]2-cyclohexeneHCID 14355054cis-2,6,6-Trimethyl-1-[1-hydroxy-2-butenyl]-1-cyclohexene

Product 1

HCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Procedure

By replacing in the above procedure cis-2,6,6-trimethyl-1-[1-hydroxy-2-butenyl]-1-cyclohexene by cis-2,6,6-trimethyl-1-[1-hydroxy-2-butenyl]-2-cyclohexene, trans-2,6,6-trimethyl-1-crotonoyl-2-cyclohexene was obtained which had the following characteristics: NMR spectrum: δ=0.83 ppm (3 H, s); 0.92 ppm, (3 H, s); 1.55 ppm, (3 H, s broad); 1.89 ppm, (d of d, J=6.5 and 1.1 cps); 1.0-2.3 ppm (4 H, complex band); 2.77 ppm, (1 H, s broad); 5.52 ppm, (1 H, s broad); 6.18 ppm, (1 H, d of q, J=16 cps and 1.1 cps); 6.77 ppm, (1 H, d of q, J=16 cps and 6.5 cps).

Sources & evidence

ORD record
ord-db9ae6ba39b640a1ba6efceb32eb443a
Source dataset
uspto-grants-1980_02
Patent number
US04187863

Reaction notes

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