Toluene → HCID 86622669, compound

HRID 1434499Notes

Reaction equation

HRID 1434499 reaction equation
[CH:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])([CH3:11])[CH2:10]1)[CH:7](O)[CH2:6][CH2:5]2)([CH3:3])[CH3:2].OS([O-])(=O)=O.[K+].[C:21]1(C)C=CC=CC=1>>[CH:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])([CH3:11])[CH2:10]1)[C:7]([CH3:21])=[CH:6][CH2:5]2)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 516920Potassium bisulfateHCID 69037673HCID 69037673, compound

Product 1

HCID 86622669HCID 86622669, compoundYield 81%

Procedure

A solution of 5-isopropyl-7,7-dimethyl-bicyclo[3.2.1]octan-2-ol (18.5 g, 88 mmol) and KHSO4 (100 mg) in toluene (250 ml) was heated 36 h in a Dean-Stark apparatus. The solution was cooled and washed once with water and brine, dried (MgSO4) and concentrated in vacuo to yield 5-isopropyl-2,7,7-trimethyl-bicyclo[3.2.1]oct-2-ene (13.77 g, 81%). 13H-NMR (100 MHz, CDCl3): 140.4 (s), 118.7 (d), 52.1 (d), 51.5 (t), 46.1 (s), 46.0 (s), 39.1 (t), 37.6 (d), 37.4 (t), 31.5 (q), 26.9 (q), 24.6 (q), 18.2 (q), 18.0 (q) ppm. GC/MS (EI): 192 (M+, 17), 177 (4), 149 (22), 136 (21), 121 (15), 107 (18), 93 (100), 77 (28), 57 (17), 41 (23). IR (ATR): 2957 s, 2933 s, 2869 m, 1468 m, 1452 m, 1366 m cm−1.

Workup

  1. temperatureThe solution was cooled
  2. washwashed once with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ff9046b6d8a45d09b09773c4ca2de5a
Source dataset
uspto-grants-2009_11
Patent number
US07615525B2

Reaction notes

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