Ethanol → HCID 19029807, compound

Temperature

100 °C

A mixture of 3-t-butylhydroxybenzoic acid (2.00 g, 10.3 mmol), benzyl bromide (6.12 mL, 52.5 mmol), KOH (3.47 g, 61.8 mmol), EtOH (60 mL), and water (6 mL) was heated at 100° C. for 48 h under nitrogen atmosphere. The reaction mixture was concentrated in vacuo and the residue was diluted with EtOH (100 mL) and water (100 mL), then stirred with KOH (3.47 g, 61.8 mmol) at 100° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with water (400 mL) and extracted with EtOAc (200 mL). The aqueous layer was acidified with 1 N HCl (10 mL) and extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4), and concentrated in vacuo to provide 4-(benzyloxy)-3-tert-butylbenzoic acid (2.36 g, 81%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 10.80 (br s, 1H), 8.08 (s, 1H), 8.07-7.94 (m, 1H), 7.45-7.34 (m, 5H), 6.99-6.96 (m, 1H), 5.20 (s, 2H), 1.42 (s, 9H); MS found: (M+H)+=285.

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionthe residue was diluted with EtOH (100 mL) and water (100 mL)
3. temperatureThe reaction mixture was cooled to room temperature
4. concentrationconcentrated in vacuo
5. additionThe residue was diluted with water (400 mL)
6. extractionextracted with EtOAc (200 mL)
7. extractionextracted with EtOAc (2×200 mL)
8. washThe combined organic layers were washed with brine (50 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo

ORD record

ord-a6d0cdde12394ea09d971ec1606c69af

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378409B2