Ammonium Chloride → 4-(1-Hydroxy-hexyl)-benzaldehyde

Temperature

0 °C

A solution of 4-diethoxymethyl-benzaldehyde (0.300 mL, 1.51 mmol) in THF (3 mL) was cooled to 0° C. Pentylmagnesium bromide (3.0 mL, 2.0M in THF, 6 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and was warmed to room temperature. Aqueous NH4Cl (satd) was added and the aqueous solution was extracted with EtOAc. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 10% aqueous acetone (50 mL) and wet Amberlyst-15 resin (1.5 g) was added. The mixture was stirred for 24 h and the resin was filtered off through Celite. The solution was concentrated in vacuo. Purification via flash chromatography (4:1 hexanes:EtOAc) provided the title compound (1.15 g). 1H NMR (400 MHz, CDCl3) δ 9.99 (s, 1H), 7.86 (d, 2H), 7.51 (d, 2H), 4.77 (m, 1H), 1.89 (m, 1H), 1.74 (m, 2H), 1.48-1.28 (m, 6H), 0.87 (m, 3H).

1. temperaturewas warmed to room temperature
2. extractionthe aqueous solution was extracted with EtOAc
3. washThe organic solution was washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in 10% aqueous acetone (50 mL)
8. additionwet Amberlyst-15 resin (1.5 g) was added
9. stirringThe mixture was stirred for 24 h
10. filtrationthe resin was filtered off through Celite
11. concentrationThe solution was concentrated in vacuo
12. customPurification via flash chromatography (4:1 hexanes:EtOAc)

ORD record

ord-c894fa18238d4e9387df607c0a844d2f

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06649657B2