2-chloroethyl benzenesulfonate

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: A mixture of 4-nitrophenol (139 g, 1 mole), 2-(benzenesulphonyloxy)ethyl chloride (220.5 g, 1 mole--see Ber. (1920), 53, 1836) and anhydrous potassium carbonate (138 g, 1 mole) in methyl ethyl ketone ("MEK"--1000 ml) was stirred at reflux for 16 hours. After cooling, the mixture was poured onto water and the organic layer was separated. Following two further extractions with methyl ethyl ketone, the combined organic fractions were dried (MgSO4), filtered and evaporated. The resultant solid was crystallised from ethanol to give the title compound, (165.8 g), m.p. 60°. at reflux for 16 hours After cooling the mixture was poured onto water the organic layer was separated two further extractions with methyl ethyl ketone the combined organic fractions were dried (MgSO4) filtered evaporated The resultant solid was crystallised from ethanol

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

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

Procedure: A mixture of 4-hydroxybenzamide (194 g, 1.25 M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8 M), and potassium carbonate (172.8 g, 1.25 M) in butan-2-one (2.16 l) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 l) was added and the resultant precipitate filtered off, washed with water, and dried. Crystallisation from ethanol gave the title compound, yield (232.0 g), m.p. 66°. at reflux for 24 hours After cooling distilled water (2.0 l) was added the resultant precipitate filtered off washed with water dried Crystallisation from ethanol

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

Procedure: A mixture of 4-hydroxybenzamide (194 g, 1.25 M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8 M), and potassium carbonate (172.8 g, 1.25 M) in butan-2-one (2.16 l) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 l) was added and the resultant precipitate filtered off, washed with water, and dried. Crystallisation from ethanol gave the title compound, yield (232.0 g), m.p. 66°. at reflux for 24 hours After cooling distilled water (2.0 l) was added the resultant precipitate filtered off washed with water dried Crystallisation from ethanol

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

Procedure: A mixture of methyl 4-hydroxybenzoate (15.2 g, 0.1 M), 2-(benzenesulphonyloxy)ethyl chloride (28.65 g, 0.12 M) and potassium carbonate (19.15 g, 0.1 M) in 4-methylpentan-2-one (170 ml) was stirred at reflux for 24 hours. After cooling, distilled water (170 ml) was added and the organic phase separated off. Evaporation to dryness gave a yellow solid which was crystallised from ethanol to give the title compound, yield (13.3 g), m.p. 56°-58°. at reflux for 24 hours After cooling distilled water (170 ml) was added the organic phase separated off Evaporation to dryness gave a yellow solid which was crystallised from ethanol

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50% Sodium hydride in mineral oil (8.11 g, 169 mmol) was added portionwise to a solution of 2-hydroxy-phenyl-acetic acid ethyl ester (30.4 g, 169 mmol) in dimethylformamide (100 ml). After the initial effervescence had ended the reaction was heated to 100° C. for 10 minutes and was cooled to room temperature. A solution of benzene sulfonic acid 2-chloro-ethyl ester (37.2 g, 169 mmol) in dimethylformamide (5 ml) was then added and the reaction was heated to 100° C. for one hour, and allowed to cool to room temperature over 18 hours. The reaction mixture was partitioned between diethylether (300 ml) and water (300 ml) and the organic phase was removed and washed with water (100 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by thermal distillation to give [2-(2-chloro-ethoxy)-phenyl]-acetic acid ethyl ester (22.0 g) as a pale yellow oil. Bp 170° C. to 180° C. νmax (thin film) 1735 cm−1 (C═O, ester); no O—H stretch. Anal. Found C, 59.35; H, 6.29. C12H15CIO3 requires C, 59.38; H, 6.23%. was cooled to room temperature the reaction was heated to 100° C. for one hour to cool to room temperature over 18 hours The reaction mixture was partitioned between diethylether (300 ml) and water (300 ml) the organic phase was removed washed with water (100 ml) dried over MgSO4 the solvent was removed under reduced pressure The residue was purified by thermal distillation

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

Procedure: 2-Chloroethanol (1168 g, 975 mol) and benzene sulfonyl chloride (2780 g, 2015 mol) were stirred together at −5° C. and pyridine (2158 g, 2200 mol) was added over a 3 hours period, maintaining the temperature below 0° C. The reaction was stirred for a further 3 hours at −5° C. to 0° C. and was then allowed to warm to room temperature over 18 hours. After pouring into a mixture of ice (10 liters) and water (10 liters) the reaction was stirred for 15 minutes, extracted with ether (10 liters) and the organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters). It was then dried over MgSO4 and concentrated under reduced pressure to give benzene sulfonic acid 2-chloro-ethyl ester (1921 g) as an orange oil. 1H NMR (250 MHz, CDCl3): δ=7.78-8.02 (2H, m), 7.58-7.78 (3H, m), 420-4.45 (2H, t), 3.60-3.81 (2H, t) ppm. maintaining the temperature below 0° C was stirred for 15 minutes extracted with ether (10 liters) the organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters) It was then dried over MgSO4 concentrated under reduced pressure

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

Procedure: 2-Chloroethanol (1168 g, 975 mol) and benzene sulfonyl chloride (2780 g, 2015 mol) were stirred together at −5° C. and pyridine (2158 g, 2200 mol) was added over a 3 hours period, maintaining the temperature below 0° C. The reaction was stirred for a further 3 hours at −5° C. to 0° C. and was then allowed to warm to room temperature over 18 hours. After pouring into a mixture of ice (10 liters) and water (10 liters) the reaction was stirred for 15 minutes, extracted with ether (10 liters) and the organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters). It was then dried over MgSO4 and concentrated under reduced pressure to give benzene sulfonic acid 2-chloro-ethyl ester (1921 g) as an orange oil. 1H NMR (250 MHz, CDCl3): δ=7.78-8.02 (2H, m), 7.58-7.78 (3H, m), 420-4.45 (2H, t), 3.60-3.81 (2H, t) ppm. maintaining the temperature below 0° C was stirred for 15 minutes extracted with ether (10 liters) the organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters) It was then dried over MgSO4 concentrated under reduced pressure

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

Procedure: A mixture of 4-hydroxybenzamide (194 g, 1.25M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8M), and potassium carbonate (172.8 g, 1.25M) in butan-2-one (2.16 1) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 1) was added and the resultant precipitate filtered off, washed with water, and dried. Crystallisation from ethanol gave the title compound, yield (232.0 g), m.p. 66°. at reflux for 24 hours After cooling distilled water (2.0 1) was added the resultant precipitate filtered off washed with water dried Crystallisation from ethanol

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

Procedure: A mixture of 4-hydroxybenzamide (194 g, 1.25M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8M), and potassium carbonate (172.8 g, 1.25M) in butan-2-one (2.16 1) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 1) was added and the resultant precipitate filtered off, washed with water, and dried. Crystallisation from ethanol gave the title compound, yield (232.0 g), m.p. 66°. at reflux for 24 hours After cooling distilled water (2.0 1) was added the resultant precipitate filtered off washed with water dried Crystallisation from ethanol