Sulfuric Acid → 4-(1-Hydroxy-2,6,6-trimethyl-cyclohex-3-en-1-yl)-but-3-yn-2-ol

Participants

Reaction Steps

5.5 g of 2-(3-oxa-pent-2-yloxy)-but-3-yne (see Example 2, letter a), 14 ml of 40% ethyl-magnesium bromide in diethyl ether and 3.5 g of 2,6,6-trimethyl-cyclohex-3-en-1-one in anhydrous diethyl ether were reacted as described in Example 2 (letter b). The crude reaction mixture was then acidified with 35% aqueous H2SO4 and stirred during 2 hours at 20°. After addition of 10% aqueous Na2CO3 until neutrality, extraction with diethyl ether, drying of the organic phase over Na2SO4 and evaporation, there were isolated 0.4 g of crude material. This latter was purified by means of crystallization in cyclohexane, m.p. 101°-104°, to give the desired compound.

Provenance & Evidence