4-Hydroxybenzaldehyde → Benzaldehyde, 4-[(2-methoxyethoxy)methoxy]-

To a solution of 4-hydroxy-benzaldehyde (3.7 g, 30 mmol) and diisopropylethylamine (7.6 mL) in CH2Cl2 (60 mL) was added MEMCl (5.0 mL) in CH2Cl2 (17 mL) dropwise at 0° C. The mixture was stirred at RT for 3 h, quenched with Hcl (60 mL, 0.5 N). The mixture was extracted with CH2Cl2. The organic phase was washed with NaOH solution (1 N) and water. The separated organic phase was dried under Na2SO4, filtered and concentrated to give 6.2 g of product (97%) which was pure enough to be used to the next reaction without further purification. 1HNMR (200 MHz, CDCl3): δ 3.36 (s, 3H), 3.54 (m, 2H), 3.83 (m, 2H), 5.41 (s, 2H), 7.16 (d, J=8.7 Hz, 2H), 7.83 (d, J=8.7 Hz, 2H), 9.90 (s, 1H).

1. customquenched with Hcl (60 mL, 0.5 N)
2. extractionThe mixture was extracted with CH2Cl2
3. washThe organic phase was washed with NaOH solution (1 N) and water
4. customThe separated organic phase was dried under Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-7cc64e0bce974a68a0bbc5713d81aeaf

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858072B2