Benzyl Bromide → 3-(Benzyloxy)benzoic acid

A solution of methyl 3-hydroxybenzoate (1.00 g, 6.56 mmol)in THF was treated with sodium hydride (60% by wt in oil, 276 mg, 6.90 mmol). After 20 minutes, the mixture was treated with benzyl bromide (0.78 mL, 6.56 mmol) and then heated at reflux. The mixture was cooled, treated with saturated ammonium chloride and EtOAc. The layers were separated and the aqueous layer was washed with EtOAc (3×). The combined organic extracts were washed with saturated NaCl, dried over MgSO4 and concentrated. A solution of the crude material in dioxane (20 mL) was treated with 2.5 N NaOR (13 mL) and stirred vigorously. The mixture was acidified by addition of 5 N HCl and partitioned with EtOAc. The aqueous layer was washed with EtOAc (3×) and the combined extracts were dried (MgSO4) and concentrated yielding the title compound.

1. temperatureheated
2. temperatureat reflux
3. temperatureThe mixture was cooled
4. customThe layers were separated
5. washthe aqueous layer was washed with EtOAc (3×)
6. washThe combined organic extracts were washed with saturated NaCl
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. additionA solution of the crude material in dioxane (20 mL) was treated with 2.5 N NaOR (13 mL)
10. additionThe mixture was acidified by addition of 5 N HCl
11. custompartitioned with EtOAc
12. washThe aqueous layer was washed with EtOAc (3×)
13. dry with materialthe combined extracts were dried (MgSO4)
14. concentrationconcentrated

ORD record

ord-1e9c0c73a8b04e6db08f0d64e36d508b

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06605626B2