3-Hydroxybenzaldehyde → HCID 10035212, compound

Participants

Reaction Conditions

Reaction Steps

A dried 1 L 3-neck flask equipped with a N2 inlet, reflux condenser, mechanical stirrer and a 500 ml drppping funnel was charged with 24.3 g (1.0 mol) of magnesium and 50 ml of anhydrous ether. To this was added 15 g (0.11 mol) of 1-bromobutane (Aldrich 23,988-7) and one crystal of iodine. The dropping funnel was charged with 122 g (0.89 mol) of 1-bromobutane and 100 ml. of anhydrous ether. After the contents of the reaction flask began to reflux, the flask was cooled with a water/ice bath and the 1-bromobutane solution was added at such a rate as to maintain a gentle reflux. After the addition was complete the reaction mixture was refluxed for one-half hour, then cooled to 0° C. in an ice/water bath. The dropping funnel was then charged with 38.0 g (0.311 mol) of 3-hydroxybenzaldehyde (Aldrich H 1,980-8) and 250 ml of anhydrous ether. This slurry was added over a 1 hour period. After the addition the reaction mixture was allowed to warm up to room temperature and was stirred overnight. The reaction mixture was neutralized with 900 ml of 5% aqueous HCl. The reaction mixture was extracted with 2×500 ml of ethyl acetate, the organic extracts combined, washed with 1L of water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate to yield 44.0 g (79%) of 1-(3-hydroxyphenyl)-1-pentanol, m.p. 120°-122° C.

Provenance & Evidence