Sodium Carbonate → 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

Participants

Reaction Conditions

Reaction Steps

To a rapidly stirred refluxing suspension of 7.5 g (0.055 mole) of zinc chloride (anhydrous) in 1000 ml of benzene there was added 304 g (2.0 moles) of α-pinene epoxide over 1.0-1.25 hour period. The resultant mixture was heated at reflux (86° C) for 1.0-1.5 hours, cooled to 25° C and then poured into 400 ml of 5% sodium carbonate solution. The aqueous layer was drawn off and the benzene layer washed twice with 400 ml of brine. The solvent was removed and the oil fractionally distilled to give campholenic aldehyde: 193.2 g (70.2% yield), bp 51°-52° C (1.5 mm); nD20 1.4658; mol wt. 152 (ms); nmr, 0.8δ (3H, s), 1.0 (3H, s), 1.6 (3H, broad s, olefinic CH3), 2.1-2.6 (4H, broad complex), 5.2 (1H, broad multiplet, olefinic H), 9.7 (1H, doublet of doublets, J~3.5 + 1.5 Hz, aldehyde H); ir, 3020, 2700, 1714, 790 cm-1.

Provenance & Evidence