2,6,6-Trimethyl-1-tetrolyl-2-cyclohexene → 2,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-2-cyclohexene

HRID 1579800Notes

Reaction equation

HRID 1579800 reaction equation
[CH3:1][C:2]1[CH:3]([C:10](=[O:14])[C:11]#[C:12][CH3:13])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1>CO>[CH3:1][C:2]1[CH:3]([CH:10]([OH:14])[C:11]#[C:12][CH3:13])[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH:7]=1

Participants

3

Reactant 1

HCID 705897112,6,6-Trimethyl-1-tetrolyl-2-cyclohexene

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The acetylenic carbinol which was obtained as described above under paragraph b) was oxidised 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-584e3ddea6b544ccbccfd29d2eedb568
Source dataset
uspto-grants-1976_01
Patent number
US03931326

Reaction notes

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