Dihydrocoumarin → 2-(3-Hydroxy-3-methylbutyl)phenol

To an ice-cooled solution of methyl magnesium bromide in ether (104 ml × 2.7M; 0.28 mole) was added slowly, under nitrogen, a solution of 13.8 g (0.093 mole) of dihydrocoumarin (Compound 28, Scheme 8) in 230 ml of dry ether. The cooling bath was then removed and the mixture stirred for a further 16 hours. The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 and the mixture was stirred to ensure dissolution. The organic layer was then separated and the aqueous layer was extracted with 2×100 ml of ether. The organic layers were combined and washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl and then dried (Na2SO4). The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a white solid. PMR (CDCl3) : & 1.30 (6H, s), 1.80 (2H, t, J~7.5 Hz), 2.12 (1H, broad s), 2.73 (2H, t, J~7.5 Hz), 6.80-6.87 (2H, m), 7.00 (1H, broad s), 7.07-7.14 (2H, m).

1. additionwas added slowly, under nitrogen
2. customThe cooling bath was then removed
3. additionThe reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4
4. stirringthe mixture was stirred
5. dissolutiondissolution
6. customThe organic layer was then separated
7. extractionthe aqueous layer was extracted with 2×100 ml of ether
8. washwashed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl
9. dry with materialdried (Na2SO4)
10. filtrationThe solution was then filtered
11. concentrationthe filtrate concentrated in-vacuo

ORD record

ord-d389777cb76147ad962fe01d03940a12

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05006550