4-pentylphenol

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:

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: 3.5 g of 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylic acid chloride [obtainable by reacting 5-n-pentylthieno[3,2-b]thiophene-5-carboxylic acid (m.p. 156°, c.p. 196°) with thionyl chloride] in 20 ml of toluene are added dropwise to a mixture of 2.25 g of 4-n-pentylphenol, 1.08 g of pyridine and 30 ml of toluene, the mixture is heated to the boil for 2 hours and allowed to cool, the pyridine hydrochloride is filtered off, and the mixture is worked up in the usual manner. 4-n-Pentylphenyl 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylate of melting point 58° and clear point 93° is obtained. the mixture is heated to the boil for 2 hours to cool the pyridine hydrochloride is filtered off

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

Procedure: 3.5 g of 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylic acid chloride [obtainable by reacting 5-n-pentylthieno[3,2-b]thiophene-5-carboxylic acid (m.p. 156°, c.p. 196°) with thionyl chloride] in 20 ml of toluene are added dropwise to a mixture of 2.25 g of 4-n-pentylphenol, 1.08 g of pyridine and 30 ml of toluene, the mixture is heated to the boil for 2 hours and allowed to cool, the pyridine hydrochloride is filtered off, and the mixture is worked up in the usual manner. 4-n-Pentylphenyl 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylate of melting point 58° and clear point 93° is obtained. the mixture is heated to the boil for 2 hours to cool the pyridine hydrochloride is filtered off

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

Procedure: To a suspension of p-pentylphenol (0.15 mole) and 2-chloro-4-hydroxybenzoic acid (0.10 mole) in toluene (500 ml.) is added concentrated sulfuric acid (0.5 g.) and boric acid (0.31 g.) (5 mole percent). The reaction mixture is refluxed for 29 hours under a Dean-Stark trap. The solvent is then removed under reduced pressure and the product is washed with ligroin. The resulting 4-pentylphenyl 2-chloro-4-hydroxybenzoate is recrystallized from an ethanol/water mixture to give 25.6 g., 81% of pure product, m.p. 149°-151°C. The reaction mixture is refluxed for 29 hours under a Dean-Stark trap The solvent is then removed under reduced pressure the product is washed with ligroin The resulting 4-pentylphenyl 2-chloro-4-hydroxybenzoate is recrystallized from an ethanol/water mixture to give 25.6 g

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

Procedure: A solution of 4-pentylphenol (20.1 g, 0.13 mol) and pyridine (10 ml, 0.13 mol) in 300 ml of methylene chloride was added under nitrogen dropwise over 45 minutes to a solution of 4-nitrophenyl chloroformate (25.28 g, 0.13 mol) in 200 ml of methylene chloride at room temperature. After the addition, the reaction was stirred overnight at room temperature. The reaction was extracted one time with 1N HCl, four times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 36.97 g of a yellow crytstalline solid. Purification of the solid on 450 g of silica gel (230-400 mesh) using 50-60% CH2Cl2 -hexane as the eluent gave 11.58 g (28%) of the title compound as a yellow crystalline solid, mp 67-69° C. After the addition The reaction was extracted one time with 1N HCl, four times with saturated Na2CO3 dried (MgSO4) the solvent removed under reduced pressure to give 36.97 g of a yellow crytstalline solid Purification of the solid on 450 g of silica gel (230-400 mesh)

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.50 g of 3-methyl-4-nitrobenzoic acid (52.5 mM) were dissolved in 400 ml of THF and 53.1 g of triethylamine (525.0 mM). The solution was cooled to −30° C. and 6.01 g of methansulfochloride (52.5 mM) were added. The mixture was stirred for 1 h at this temperature, then a solution of 8.21 g of 4-pentylphenol (50.0 mM) in 20 ml of THF was added, followed by 100 mg of DMAP. The reaction mixture was stirred for 1 h at −30° C. and was allowed to warm to room temperature while stirred overnight. The next day, the mixture was filtered through a pad of celite filter aid, evaporated to dryness. The residue was flash chromatographed on silica gel using cyclohexane/ethyl acetate: 1/1 as eluent to afford 4-pentylphenyl 3-methyl-4-nitrobenzoate as a yellow oil. Yield: 16.2 g (49.5 mM, 99%). 6.01 g of methansulfochloride (52.5 mM) were added The reaction mixture was stirred for 1 h at −30° C. to warm to room temperature while stirred overnight The next day, the mixture was filtered through a pad of celite filter aid evaporated to dryness chromatographed on silica gel