Water → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

Temperature

80 °C

3-Hydroxy-2,2-dimethyl-propionic acid methyl ester (3.00 g, 22.7 mmol) in 40 mL of THF at 0° C. was treated with 1.0 g (25 mmol) of 60% NaH in mineral oil for 20 min. Benzyl bromide (2.97 mL, 25.0 mmol) was added dropwise over 10 minutes. The mixture was stirred overnight, 30 mL of water was added, and the mixture was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine, dried with MgSO4, filtered, and concentrated. The residue was dissolved in 40 mL of EtOH, 28 mL of 2M NaOH was added, and the mixture was heated to 80° C. for 12 h. The mixture was cooled, neutralized with 2M HCl, and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine, dried with MgSO4, filtered, concentrated, and chromatographed (10-100% EtOAc in hexanes) to provide 2.4 g of 3-benzyloxy-2,2-dimethyl-propionic acid.

1. extractionthe mixture was extracted with EtOAc (3×100 mL)
2. washThe combined extracts were washed with brine
3. dry with materialdried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in 40 mL of EtOH
7. addition28 mL of 2M NaOH was added
8. temperatureThe mixture was cooled
9. extractionextracted with EtOAc (3×100 mL)
10. washThe combined extracts were washed with brine
11. dry with materialdried with MgSO4
12. filtrationfiltered
13. concentrationconcentrated
14. customchromatographed (10-100% EtOAc in hexanes)

ORD record

ord-c04fe54426fa4889a1cb18fa2f81e9e3

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514458B2