Water → 4-Methoxy-alpha,alpha-dimethylbenzyl alcohol

Temperature

12.5 °C

This was synthesized using a synthesis based on that described by Archer et al., J. Org. Chem., Vol. 42, No. 13, 1977, page 2282, column 2 (see synthesis of (22)). A solution of 4-methoxy acetophenone (151.18 g, 1 mol) in 300 ml of anhydrous THF was added for 1 h to the solution of 1N methyl magnesium chloride (1360 ml, 1.36 mol) in THF while maintaining the internal temperature at 10-15° C. After completion of the addition, the reaction mixture was heated for about 4.5 hrs. After completion of the reaction (as determined by TLC), 0.2 L of water was slowly added during 3 hrs to quench the reaction while maintaining the internal temperature at <15° C. The reaction mixture was decanted from the precipitate and evaporated under vacuum. The remaining white residue was washed with methyl t-butyl ether (MTBE) (2×200 mL) and evaporated. The combined residue was dissolved in 400 mL of MTBE and 200 mL of water was added. The organic layer was extracted and the aqueous layer was washed with MTBE (3×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate and evaporated to dryness to afford 156 g of 2-(4-Methoxy-phenyl)-propan-2-ol as yellow oil (94% yield, 96% purity by HPLC).

1. customThis was synthesized
2. additionAfter completion of the addition
3. temperaturethe reaction mixture was heated for about 4.5 hrs
4. additionwas slowly added during 3 hrs
5. customto quench
6. customthe reaction
7. temperaturewhile maintaining the internal temperature at <15° C
8. customThe reaction mixture was decanted from the precipitate
9. customevaporated under vacuum
10. washThe remaining white residue was washed with methyl t-butyl ether (MTBE) (2×200 mL)
11. customevaporated
12. dissolutionThe combined residue was dissolved in 400 mL of MTBE
13. addition200 mL of water was added
14. extractionThe organic layer was extracted
15. washthe aqueous layer was washed with MTBE (3×50 mL)
16. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
17. customevaporated to dryness

ORD record

ord-d4379f371bdc4baba3643a1b5680f6b3

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258322B2