Hydrochloric Acid → 2-(Benzyloxy)-5-formylbenzoic acid

Lithium hydroxide (3.38 g, 0.14 mol, 3 eq) in water (50 mL) was added to a stirred solution of benzyl 2-benzyloxy-5-formylbenzoate (16.13 g, 0.046 mol, 1 eq) in a mixture of tetrahydrofuran (200 mL) and methanol (50 mL). The solution was stirred overnight, acidified to pH 1 with 10% HCl, and the organic solvents removed in vacuo. The aqueous solution was extracted with ethyl acetate (200 mL), and the organic solution washed with brine (200 mL), then extracted with saturated aqueous sodium bicarbonate (3×200 mL). The basic solution was washed with ethyl acetate (200 mL), then acidified to pH 1 with 10% HCl and back extracted with ethyl acetate (3×200 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a pale yellow powder (10.83 g, 89%). 1H NMR (CDCl3) δ9.94 (s, 1H, O═C—H), 5.37 (s, 2H, CH2Ph).

1. customthe organic solvents removed in vacuo
2. extractionThe aqueous solution was extracted with ethyl acetate (200 mL)
3. washthe organic solution washed with brine (200 mL)
4. extractionextracted with saturated aqueous sodium bicarbonate (3×200 mL)
5. washThe basic solution was washed with ethyl acetate (200 mL)
6. extractionback extracted with ethyl acetate (3×200 mL)
7. dry with materialThe organic solution was dried over sodium sulfate
8. customevaporated in vacuo

ORD record

ord-5e60264d103a4e73a4ffcfeb870d4a01

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06740670B2