Ethanol → 127049-37-0

Temperature

80 °C

80 mmol t-butylhydroquinone together with 80 mmol potassium bromate is suspended in 100 ml water. 20 drops 1 M sulfuric acid is added thereto while stirring. The reaction mixture is slowly heated to 80° C. while stirring. A clear orange solution of the quinone forms. When this is cooled to room temperature orange needles precipitate (t-butylbenzoquinone). These are dissolved in 400 ml ethanol while still wet. The solution is irradiated for 15 h at 5° C. with a 250 W sodium-vapour lamp (TLC control). The solvent is removed by distillation, the residue is washed with toluene/hexane 1:1. The remaining colourless crystalline residue (2-(2'-ethyl-2'-ethoxy-propyl)-hydroquinone) is fed into a mixture of 4 ml ethanol and 80 ml glacial acetic acid. 4 ml 40% aqueous tetrafluoroboric acid is added while stirring. The mixture is heated to 80° C. during which a clear solution forms. After cooling to room temperature it is poured onto 200 ml water and extracted with toluene. The organic phase is washed once with water and dried over potassium carbonate. After removing the solvent by distillation an oil remains (5-hydroxy-2,2-dimethyl-2,3-dihydro-benzofurane). The benzoylation, oxidation and saponification are carried out as described in example 15.

1. stirringwhile stirring
2. customThe solvent is removed by distillation
3. washthe residue is washed with toluene/hexane 1:1
4. additionThe remaining colourless crystalline residue (2-(2'-ethyl-2'-ethoxy-propyl)-hydroquinone) is fed into a mixture of 4 ml ethanol and 80 ml glacial acetic acid
5. addition4 ml 40% aqueous tetrafluoroboric acid is added
6. stirringwhile stirring
7. temperatureThe mixture is heated to 80° C. during which a clear solution forms
8. temperatureAfter cooling to room temperature it
9. additionis poured onto 200 ml water
10. extractionextracted with toluene
11. washThe organic phase is washed once with water
12. dry with materialdried over potassium carbonate
13. customAfter removing the solvent
14. distillationby distillation an oil

ORD record

ord-ba5c1c1dcd7c4fe7b0b35e81763568cb

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06107036