4-Hydroxybenzaldehyde → HCID 56925554, compound

Temperature

0 °C

To a solution of 3-methyl-1-pentyn-3-ol 6 (0.319 mL, 2.83 mmol) in acetonitrile (3 mL) at 0° C. was added DBU (0.55 mL, 3.69 mmol). Then TFAA (0.34 mL, 2.46 mmol) was added drop wise and the solution was stirred at 0° C. for 30 min. To a solution of 4-hydroxybenzaldehyde (300 mg, 2.46 mmol) in acetonitrile at 0° C. was added DBU (0.55 mL 3.69 mmol) and CuCl2.2H2O (0.42 mg, 0.0025 mmol). The first mixture was added to the second mixture over a period of five min. The reaction was stirred overnight. The solvent was removed by rotary evaporation and the residue diluted with DCM. Then the organic layer washed with 1M HCl, 1M NaOH, sat NaHCO3 and brine, dried over MgSO4 and concentrated in vacuum to give 170 mg (32%) of product. 1H NMR (CDCl3): δ 9.91 (s, 1H), 7.83-7.81 (m, 2H), 7.36-7.34 (m, 2H), 2.69 (s, 1H), 2.06-1.92 (m, 2H), 1.66 (s, 3H), 1.12 ppm (t, J=7.2 Hz, 3H).

1. additionThe first mixture was added to the second mixture over a period of five min
2. stirringThe reaction was stirred overnight
3. customThe solvent was removed by rotary evaporation
4. additionthe residue diluted with DCM
5. washThen the organic layer washed with 1M HCl, 1M NaOH
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuum

ORD record

ord-4bc6820a35bf45dea4f08702b3d24deb

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062072B2