p-Toluenesulfonic acid → HCID 22914105, compound

HRID 1377433Notes

Reaction equation

HRID 1377433 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH:8]([CH2:11][C:12]([CH3:14])=[CH2:13])[CH2:9][OH:10].CC1C=CC(S(O)(=O)=O)=CC=1>CCCCCC>[CH3:13][C:12]1([CH3:14])[CH2:11][CH:8]([CH:3]2[CH2:4][CH:5]=[C:6]([CH3:7])[C:2]2([CH3:15])[CH3:1])[CH2:9][O:10]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22914122HCID 22914122, compound

Product 1

HCID 22914105HCID 22914105, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 500 ml 3 neck round bottomed flask was charged with 56.1 g of 2-(2,2,3-trimethylcyclopent-3-en-1-yl)-4-methyl-4-pentenol, (0.26 mole), 260 ml of hexane, and 0.75 g of p-TSA. The mixture was then refluxed for 7 hours. After cooling the batch was washed with 250 ml of 10% sodium carbonate, and once with 250 ml of brine. The batch was dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product was distilled through a 10 cm micro Vigreaux column to afford 49.6 g of purified product (90% yield). BP 51°-52° C./0.2 mmHg; 1H-NMR (300 MHz), δ 0.85 (3H, s), 0.95 (3H, s), 1.22 (3H, s), 1.27 (3H, s), 1.45 (1H, m), 1.58 (3H, s), 1.73 (1H, m), 1.83-2.0 (2H, m), 2.15 (1H, m), 2.40 (1H, m), 3.46 (1H, m, B part of ABX, JAB =6.63 Hz, JBX =6.63 Hz), 4.07 (1H, t, A part of ABX, JAB =6.63 Hz, JAX =6.63 Hz), 5.21 (1H, s), 13C-NMR (75 MHz), δ 12.59, 19.93, 26.57, 28.87, 29.09, 35.42, 42.06, 45.82, 47.09, 54.39, 72.08, 79.67, 121.98, 149.07; IR (Neat), 2980, 1055 cm-1 ; MS (m/e), 208 (M+), 193, 177, 43 (Base);

Workup

  1. temperatureThe mixture was then refluxed for 7 hours
  2. temperatureAfter cooling the batch
  3. washwas washed with 250 ml of 10% sodium carbonate
  4. dry with materialThe batch was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationThe crude product was distilled through a 10 cm micro Vigreaux column

Sources & evidence

ORD record
ord-169537f79a5a424da880ed6df9f83042
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

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