2,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-2-cyclohexene → (Z)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

HRID 903293Notes

Reaction equation

HRID 903293 reaction equation
[CH3:1][C:2]1[CH:3]([CH:10]([OH:14])[C:11]#[C:12][CH3:13])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1.CC1C(C(=O)C#CC)C(C)(C)CCC=1>CO>[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

4

Reactant 2

HCID 129319252,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-2-cyclohexeneHCID 705897112,6,6-Trimethyl-1-tetrolyl-2-cyclohexene

Product 1

HCID 6436548(Z)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The acetylenic carbinol which was obtained as described above under paragraph (b) was oxidized as described for its isomer in Example 18, paragraph (c). Thus, 1.38 g. of carbinol gave 0.9 g. (66%) of 2,6,6-trimethyl-1-tetrolyl-2-cyclohexene, b.p. 100°-105°/0.7 Torr. NMR spectrum (CCl4): 0.96 (6 H, d badly resolved), 1.52 (3 H, m), 2.0 (3 H, s), 5.57 (1 H, m), 2.66 (1 H, m) ppm (δ).

Sources & evidence

ORD record
ord-e5507779a1c94c90b54e146fcc1fc66b
Source dataset
uspto-grants-1980_10
Patent number
US04226892

Reaction notes

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