3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl- → 2,2,3-Trimethylcyclopentaneacetaldehyde

HRID 1721273Notes

Reaction equation

HRID 1721273 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH2:8][CH:9]=[O:10]>[Pd]>[CH3:11][C:2]1([CH3:1])[CH:6]([CH3:7])[CH2:5][CH2:4][CH:3]1[CH2:8][CH:9]=[O:10]

Participants

3

Reactant 1

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

Product 1

HCID 224142552,2,3-Trimethylcyclopentaneacetaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

510 g of 2-(2,2,3-trimethylcyclopent-3-en-1-yl) acetaldehyde at 85% (2.85 moles) were hydrogenated with 20 g of 5% Pd on carbon (50% wet) with 10 g of soda ash at 60 psi and 50°-60° C. The crude product was distilled from 22 g of boric anhydride affording 324 g of purified product, containing pinocamphone as a 10-15% impurity. BP 48° C./0.6 mmHg; 1H-NMR (300 MHz), δ0.54 (3H, s), 0.87 (3H, d, J=6.6 Hz), 0.88 (3H, s), 1.1-1.4 (2H, m), 2.25 (1H, m), 2.50 (1H, m), 2.55 (1H, m), 2.70-2.95 (3H, br m), 9.76 (1H, br s); 13C-NMR (75 MHz), δ14.01, 14.73, 25.54, 28.34, 30.35, 42.62, 44.84, 45.03, 45.75, 203.83; IR (Neat), 2980, 2720, 1730, 1470, 1390, 1370 cm-1 ; MS (m/e), 139 (M+ -15), 97, 69 (Base).

Workup

  1. distillationThe crude product was distilled from 22 g of boric anhydride affording 324 g of purified product
  2. additioncontaining pinocamphone as a 10-15% impurity

Sources & evidence

ORD record
ord-43370e6dd7484748a01d3853f4b6730d
Source dataset
uspto-grants-1996_04
Patent number
US05510326

Reaction notes

Loading…