Butyl bromide → HCID 22420383, compound

A mixture of methyl 5-(4-hydroxybenzoyl)pentanoate (2 g), acetone (50 ml), potassium carbonate (2.34 g), and 1-bromobutane (2.0 ml) is gently refluxed for 4 hours. The reaction mixture is filtered and the filtrate concentrated in vacuo. The resulting brown solid is dissolved in ethanol (25 ml) and 2N sodium hydroxide (25 ml), and then refluxed for 4 hours. After washing with ether (100 ml), the aqueous layer is acidified to pH 1.0 with concentrated hydrochloric acid and the product extracted with ether (1×300 ml). The ether solution is dried over magnesium sulfate, filtered, and concentrated in vacuo. The product is recrystallized from ethanol/water to yield 5-(4-n-butoxybenzoyl)pentanoic acid (1.2 g), m.p. 95° C.

1. temperatureis gently refluxed for 4 hours
2. filtrationThe reaction mixture is filtered
3. concentrationthe filtrate concentrated in vacuo
4. dissolutionThe resulting brown solid is dissolved in ethanol (25 ml)
5. temperature2N sodium hydroxide (25 ml), and then refluxed for 4 hours
6. washAfter washing with ether (100 ml)
7. extractionthe product extracted with ether (1×300 ml)
8. dry with materialThe ether solution is dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe product is recrystallized from ethanol/water

ORD record

ord-6b416d8cdd1345f2aaea141e7baec7d3

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05504244