3-ethylcatechol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium chloride (1.71 g, 18 mmol) was added at room temperature to a solution of 10 (1 g, 7.2 mmol) in acetonitrile (10 mL), followed by triethylamine (6.3 mL, 45 mmol). Paraformaldehyde (1.47 g, 49 mmol) was then added portionwise to the stirred suspension and the mixture was heated at reflux for 2 hours. The mixture was cooled to room temperature then poured into a vigorously stirred mixture of 50 mL of 5% HCl and 50 mL of diethyl ether. The organic phase was separated, and the aqueous layer re-extracted with 50 mL of ether. The combined organic extracts were washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1) to give 0.9 g of 11: the mixture was heated at reflux for 2 hours The organic phase was separated the aqueous layer re-extracted with 50 mL of ether The combined organic extracts were washed with brine dried over sodium sulphate the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of crude 9 (ca. 80 mmol) in 2N NaOH (40 mL) cooled to 0-5° C., a solution of ca. 7% hydrogen peroxide (49 mL) was added dropwise over 30 min while maintaining the temperature at 20° C. The reaction was stirred for further 45 min then diluted with AcOEt (ca 250 mL), washed with HCl 2N (ca 50 mL). The aqueous layer was e-extracted with AcOEt and the combined organic extracts were washed with brine, and dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was columned (cyclohexane:AcOEt 4:1) to give 6.4 g of 10 as a brown oil: washed with HCl 2N (ca 50 mL) the combined organic extracts were washed with brine dried over sodium sulphate The solvent was removed under reduced pressure to give a crude which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium chloride (1.71 g, 18 mmol) was added at room temperature to a solution of 10 (1 g, 7.2 mmol) in acetonitrile (10 mL), followed by triethylamine (6.3 mL, 45 mmol). Paraformaldehyde (1.47 g, 49 mmol) was then added portionwise to the stirred suspension and the mixture was heated at reflux for 2 hours. The mixture was cooled to room temperature then poured into a vigorously stirred mixture of 50 mL of 5% HCl and 50 mL of diethyl ether. The organic phase was separated, and the aqueous layer re-extracted with 50 mL of ether. The combined organic extracts were washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1) to give 0.9 g of 11: the mixture was heated at reflux for 2 hours The organic phase was separated the aqueous layer re-extracted with 50 mL of ether The combined organic extracts were washed with brine dried over sodium sulphate the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of crude 9 (ca. 80 mmol) in 2N NaOH (40 mL) cooled to 0-5° C., a solution of ca. 7% hydrogen peroxide (49 mL) was added dropwise over 30 min while maintaining the temperature at 20° C. The reaction was stirred for further 45 min then diluted with AcOEt (ca 250 mL), washed with HCl 2N (ca 50 mL). The aqueous layer was e-extracted with AcOEt and the combined organic extracts were washed with brine, and dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was columned (cyclohexane:AcOEt 4:1) to give 6.4 g of 10 as a brown oil: washed with HCl 2N (ca 50 mL) the combined organic extracts were washed with brine dried over sodium sulphate The solvent was removed under reduced pressure to give a crude which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium chloride (1.71 g, 18 mmol) was added at room temperature to a solution of 10 (1 g, 7.2 mmol) in acetonitrile (10 mL), followed by triethylamine (6.3 mL, 45 mmol). Paraformaldehyde (1.47 g, 49 mmol) was then added portionwise to the stirred suspension and the mixture was heated at reflux for 2 hours. The mixture was cooled to room temperature then poured into a vigorously stirred mixture of 50 mL of 5% HCl and 50 mL of diethyl ether. The organic phase was separated, and the aqueous layer re-extracted with 50 mL of ether. The combined organic extracts were washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1) to give 0.9 g of 11: the mixture was heated at reflux for 2 hours The organic phase was separated the aqueous layer re-extracted with 50 mL of ether The combined organic extracts were washed with brine dried over sodium sulphate the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:1)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of crude 9 (ca. 80 mmol) in 2N NaOH (40 mL) cooled to 0-5° C., a solution of ca. 7% hydrogen peroxide (49 mL) was added dropwise over 30 min while maintaining the temperature at 20° C. The reaction was stirred for further 45 min then diluted with AcOEt (ca 250 mL), washed with HCl 2N (ca 50 mL). The aqueous layer was e-extracted with AcOEt and the combined organic extracts were washed with brine, and dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was columned (cyclohexane:AcOEt 4:1) to give 6.4 g of 10 as a brown oil: washed with HCl 2N (ca 50 mL) the combined organic extracts were washed with brine dried over sodium sulphate The solvent was removed under reduced pressure to give a crude which