5-pentylbenzene-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:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of olivetol (3.6 g, 20 mmol), zinc chloride (3.5 g, 26 mmol), water (3.5 mL, 19 mmol) and dichloromethane (35 mL) was refluxed for 1 hour. A solution of (−)-p-mentha-2,8-dien-1-ol (3.0 g, 20 mmol) in dichloromethane (10 mL) was added drop-wise over 0.75 hour to the refluxing mixture, and the resultant reaction mixture was mixed for 0.5 hours at reflux. The mixture was cooled to 25° C., ice water (50 mL) was added, and the resultant biphasic mixture stirred for 20 minutes at 0° C. The resultant organic phase was collected, washed with water (2×20 mL) and 5% NaHCO3 (20 mL). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 6.0 g of first crude (+)-CBD residue. Analysis (GC) of the first crude (+)-CBD residue indicated that it contained (+)-CBD (46.9%) and abn-(−)-CBD (19.7%). The first crude (+)-CBD residue was purified by column chromatography on silica gel (eluent MTBE/hexane) to provide 2.4 g of a second crude (+)-CBD residue. was refluxed for 1 hour the resultant reaction mixture was mixed for 0.5 hours at reflux The resultant organic phase was collected washed with water (2×20 mL) and 5% NaHCO3 (20 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure

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

Procedure: 5-n-Pentyl resorcinol is reacted with methyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate to produce 1,2-dihydro-9-hydroxy-2-methyl-7-n-pentyl-4-oxo-4H-thieno[2,3-c][1] benzopyran, m.p. 188°-190°C, in 62% yield.

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

Procedure: 5-n-Pentyl resorcinol is reacted with methyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate to produce 1,2-dihydro-9-hydroxy-2-methyl-7-n-pentyl-4-oxo-4H-thieno[2,3-c][1] benzopyran, m.p. 188°-190°C, in 62% yield.

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

Procedure: Ethyl 5,5-dimethyl-3-oxo-tetrahydrothiophene-2-carboxylate was reacted with 5-n-pentyl resorcinol following a procedure similar to that of Example 3-C to produce 1,2-dihydro-2,2-dimethyl-9-hydroxy-7-n-pentyl-4-oxo-4H-thieno-[2,3-c][1] benzopyran in a 72.5% yield, m.p. 203°-206°C.

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

Procedure: Ethyl 5,5-dimethyl-3-oxo-tetrahydrothiophene-2-carboxylate was reacted with 5-n-pentyl resorcinol following a procedure similar to that of Example 3-C to produce 1,2-dihydro-2,2-dimethyl-9-hydroxy-7-n-pentyl-4-oxo-4H-thieno-[2,3-c][1] benzopyran in a 72.5% yield, m.p. 203°-206°C.

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

Procedure: Olivetol (49.5 g, 261 mmol) and ethyl 2-oxocyclohexanecarboxylate (47.7 ml, 285 mmol) were initially introduced in toluene and, after addition of 28.8 ml (310 mmol) of phosphoryl chloride, were stirred at room temp. for 38 h. The reaction mixture was slowly poured into 400 ml of water and stirred vigorously for 30 min. The precipitated yellow solid was filtered off and washed with water and toluene. The pale-yellow solid was taken up in hot ethyl methyl ketone, washed with aqueous saturated sodium hydrogencarbonate soln. solution and sat. sodium chloride solution, dried over sodium sulfate, filtered and evaporated in vacuo. Crystallisation of the crude product from acetonitrile/toluene gave 32.7 g (82%) of 1-hydroxy-3-pentyl-7,8,9,10-tetra-hydrobenzo[c]chromen-6-one as colourless crystals. stirred vigorously for 30 min The precipitated yellow solid was filtered off washed with water and toluene washed with aqueous saturated sodium hydrogencarbonate soln solution and sat. sodium chloride solution, dried over sodium sulfate filtered evaporated in vacuo Crystallisation of the crude product from acetonitrile/toluene

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

Procedure: Geraniol (3 g, 0.0194 mol) and olivetol (2 g, 0.0111 mol) were dissolved in 400 mL of chloroform containing 80 mg of p-toluenesulfonic acid as catalyst and the reaction mixture was stirred at room temperature for 12 h in the dark. After 12 hours, the reaction mixture was washed with saturated sodium bicarbonate (400 mL) and then with H2O (400 mL). The chloroform layer was concentrated at 40 C under reduced pressure, and the residue obtained was chromatographed on a 2.0 cm×25 cm silica gel column using benzene (1000 mL) as the eluent to give 1.4 g (0.00442 mol)(39.9%) CBG as product. After 12 hours the reaction mixture was washed with saturated sodium bicarbonate (400 mL) The chloroform layer was concentrated at 40 C under reduced pressure the residue obtained was chromatographed on a 2.0 cm×25 cm silica gel column to give 1.4 g (0.00442 mol)(39.9%) CBG as product

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

Procedure: Geraniol (3 g, 0.0194 mol) and olivetol (2 g, 0.0111 mol) were dissolved in 400 mL of chloroform containing 80 mg of p-toluenesulfonic acid as catalyst and the reaction mixture was stirred at room temperature for 12 h in the dark. After 12 hours, the reaction mixture was washed with saturated sodium bicarbonate (400 mL) and then with H2O (400 mL). The chloroform layer was concentrated at 40 C under reduced pressure, and the residue obtained was chromatographed on a 2.0 cm×25 cm silica gel column using benzene (1000 mL) as the eluent to give 1.4 g (0.00442 mol)(39.9%) CBG as product. After 12 hours the reaction mixture was washed with saturated sodium bicarbonate (400 mL) The chloroform layer was concentrated at 40 C under reduced pressure the residue obtained was chromatographed on a 2.0 cm×25 cm silica gel column to give 1.4 g (0.00442 mol)(39.9%) CBG as product

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of olivetol (3.6 g, 20 mmol), zinc chloride (3.5 g, 26 mmol), water (3.5 mL, 19 mmol) and dichloromethane (35 mL) was refluxed for 1 hour. A solution of (−)-p-mentha-2,8-dien-1-ol (3.0 g, 20 mmol) in dichloromethane (10 mL) was added drop-wise over 0.75 hour to the refluxing mixture, and the resultant reaction mixture was mixed for 0.5 hours at reflux. The mixture was cooled to 25° C., ice water (50 mL) was added, and the resultant biphasic mixture stirred for 20 minutes at 0° C. The resultant organic phase was collected, washed with water (2×20 mL) and 5% NaHCO3 (20 mL). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 6.0 g of first crude (+)-CBD residue. Analysis (GC) of the first crude (+)-CBD residue indicated that it contained (+)-CBD (46.9%) and abn-(−)-CBD (19.7%). The first crude (+)-CBD residue was purified by column chromatography on silica gel (eluent MTBE/hexane) to provide 2.4 g of a second crude (+)-CBD residue. was refluxed for 1 hour the resultant reaction mixture was mixed for 0.5 hours at reflux The resultant organic phase was collected washed with water (2×20 mL) and 5% NaHCO3 (20 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure