HCID 13952038, compound → HCID 54171761, compound

HRID 903291Notes

Reaction equation

HRID 903291 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])[C:11]#[C:12][CH3:13]>O=[Mn]=O>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[C:10](=[O:14])[C:11]#[C:12][CH3:13]

Participants

3

Reactant 1

HCID 13952038HCID 13952038, compound

Product 1

HCID 54171761HCID 54171761, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

A mixture of 1.277 g. (66.3 mMole) of the acetylenic carbonyl compound prepared according to the description of paragraph (b) above, 12 g. of activated MnO2 and 100 ml. of petroleum-ether (30°-40°) were stirred for 15 minutes at room temperature. The solid was removed by filtration and the liquid was dried over molecular sieves then it was concentrated and distilled under reduced pressure. 1.02 g. (81%) of 2,6,6-trimethyl-1-tetrolyl-1-cyclohexene were thus obtained, the analytical measurements thereof gave the following results: nD20 =1.5107; d420 =0.957. IR spectrum (liquid phase): 2210 (νC↓C), 1640 (νC=0)cm-1. NMR spectrum (CCl4): 1.08 (3 H, s), 1.68 (3 H, s), 2.02 (3 H, s) ppm (δ). Mass spectrum: 190 (28), 175(100), 67 (63), 123 (37), 41 (25), 81 (24), 135 (22), 28 (21), 91 (20), 147 (20).

Workup

  1. additionA mixture of 1.277 g
  2. customThe solid was removed by filtration
  3. customthe liquid was dried over molecular sieves
  4. concentrationit was concentrated
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e191604ceb7b4f6f981a39cfcef5dac5
Source dataset
uspto-grants-1980_10
Patent number
US04226892

Reaction notes

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