Isobutylene oxide → HCID 60886089, compound

Temperature

150 °C

Methyl(4-hydroxyphenyl)acetate (500 mg, 3.0 mmol) was dissolved in DMF (3 mL). K2CO3 (829 mg, 6.0 mmol) was added followed by isobutylene oxide (800 μL, 9.0 mmol). The mixture was heated to 150° C. by microwave irradiation for 30 min and concentrated. The residue was dissolved in a 1:1 mixture of methanol and water (20 mL). NaOH (1 g) was added and the mixture was stirred for 30 min. Methanol was removed by rotary evaporation. The aqueous phase was acidified by 4 M HCl and extracted with dichloromethane (2×50 mL). The combined organic phases were extracted with 2 M NaOH (2×50 mL). The combined aqueous phases were subsequently acidified by 4 M HCl and extracted with dichloromethane (2×50 mL). The combined organic phases were dried over Na2SO4, filtered and evaporated to afford [4-(2-hydroxy-2-methylpropoxy)phenyl]acetic acid (106MBT52-D, 470 mg, 70%) as a colourless solid. 1H-NMR (CDCl3): δ 7.19 (m, 2H), 6.88 (m, 2H), 3.78 (s, 2H), 3.57 (s, 2H), 1.34 (s. 6H).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in a 1:1 mixture of methanol and water (20 mL)
3. additionNaOH (1 g) was added
4. customMethanol was removed by rotary evaporation
5. extractionextracted with dichloromethane (2×50 mL)
6. extractionThe combined organic phases were extracted with 2 M NaOH (2×50 mL)
7. extractionextracted with dichloromethane (2×50 mL)
8. dry with materialThe combined organic phases were dried over Na2SO4
9. filtrationfiltered
10. customevaporated

ORD record

ord-59b82a6235a54264ad5536477a2cef7a

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476682B2