4-propan-2-ylbenzene-1,3-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4-Isopropyl-benzene-1,3-diol (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at RT for 10 min. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 h. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at RT for 4 h before. The reaction mixture was extracted with ethyl acetate (300 ml) and washed with sat. sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane). equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at 90° C. for 16 h was stirred at RT for 4 h before The reaction mixture was extracted with ethyl acetate (300 ml) washed with sat. sodium bicarbonate (100 ml) the organic layer was dried over sodium sulphate The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)

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

Procedure: 4-Isopropyl-benzene-1,3-diol (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at RT for 10 min. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 h. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at RT for 4 h before. The reaction mixture was extracted with ethyl acetate (300 ml) and washed with sat. sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane). equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at 90° C. for 16 h was stirred at RT for 4 h before The reaction mixture was extracted with ethyl acetate (300 ml) washed with sat. sodium bicarbonate (100 ml) the organic layer was dried over sodium sulphate The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Isopropyl-benzene-1,3-diol (1 eq) was taken up in BF3.OEt2 (6 eq) and acetic acid was added (2 eq). The solution was heated for 16 hours at 90° C. than allowed to cool to room temperature. The solution was added drop wise to 10% NaOAc (aq) and allowed to stand for 4 hours, before being extracted in to EtOAc. The organic phases were combined and washed with sat. NaHCO3 (aq), then dried over MgSO4, filtered and concentrated in vacuo. The residual oil was purified by column chromatography, eluting with dichloromethane, to give 1-(2,4-Dihydroxy-5-isopropyl-phenyl)-ethanone as a white solid. to cool to room temperature before being extracted in to EtOAc washed with sat. NaHCO3 (aq) dried over MgSO4 filtered concentrated in vacuo The residual oil was purified by column chromatography eluting with dichloromethane

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

Procedure: 2,4-Bis-benzyloxy-1-isopropenyl-benzene was taken up in solution in ethanol and added to 10% palladium on carbon, which had been pre-wetted with water. Hydrogen was introduced to the flask and the mixture was allowed to shake for 16 hours. The catalyst was filtered from the reaction mixture, by a suitable method, and the liquor was concentrated in vacuo, to give 4-isopropyl-benzene-1,3-diol as a white crystalline solid. The catalyst was filtered from the reaction mixture, by a suitable method the liquor was concentrated in vacuo

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

Procedure: 4-Isopropyl-benzene-1,3-diol (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at RT for 10 min. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 h. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at RT for 4 h before. The reaction mixture was extracted with ethyl acetate (300 ml) and washed with sat. sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane). equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at 90° C. for 16 h was stirred at RT for 4 h before The reaction mixture was extracted with ethyl acetate (300 ml) washed with sat. sodium bicarbonate (100 ml) the organic layer was dried over sodium sulphate The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a tetrahydrofuran solution (10 ml) of 4-isopropylresorcinol (466 mg), sodium hydride (60% dispersion in liquid paraffin) (269 mg) was added and stirred at 0° C. for 30 minutes. Then, dibenzyl chlorophosphate (10 w/v % solution in benzene) (20 ml) was added dropwise. After stirring at room temperature for 3 hours, water (30 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (20 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.23 g) was subjected to silica gel chromatography (silica gel 76 g, chloroform to chloroform:methanol=70:1), to give 1,3-bis(dibenzylphosphonooxy)-4-isopropylbenzene (1.71 g, yield: 83%) as a yellow liquid. After stirring at room temperature for 3 hours the extraction Then, the extract was washed with saturated brine (20 ml) dried with anhydrous sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a tetrahydrofuran solution (10 ml) of 4-isopropylresorcinol (466 mg), sodium hydride (60% dispersion in liquid paraffin) (269 mg) was added and stirred at 0° C. for 30 minutes. Then, dibenzyl chlorophosphate (10 w/v % solution in benzene) (20 ml) was added dropwise. After stirring at room temperature for 3 hours, water (30 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (20 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.23 g) was subjected to silica gel chromatography (silica gel 76 g, chloroform to chloroform:methanol=70:1), to give 1,3-bis(dibenzylphosphonooxy)-4-isopropylbenzene (1.71 g, yield: 83%) as a yellow liquid. After stirring at room temperature for 3 hours the extraction Then, the extract was washed with saturated brine (20 ml) dried with anhydrous sodium sulfate concentrated

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

Procedure: 4-Isopropyl-benzene-1,3-diol (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at RT for 10 min. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 h. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at RT for 4 h before. The reaction mixture was extracted with ethyl acetate (300 ml) and washed with sat. sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane). equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at 90° C. for 16 h was stirred at RT for 4 h before The reaction mixture was extracted with ethyl acetate (300 ml) washed with sat. sodium bicarbonate (100 ml) the organic layer was dried over sodium sulphate The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)

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

Procedure: 4-Isopropyl-benzene-1,3-diol (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at RT for 10 min. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 h. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at RT for 4 h before. The reaction mixture was extracted with ethyl acetate (300 ml) and washed with sat. sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane). equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at 90° C. for 16 h was stirred at RT for 4 h before The reaction mixture was extracted with ethyl acetate (300 ml) washed with sat. sodium bicarbonate (100 ml) the organic layer was dried over sodium sulphate The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)