2-phenylbutanoyl chloride

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:

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

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

Procedure: A solution of 2-phenylbutyryl chloride (1.19 g, 6.5 mmol) in 5 mL of THF was added to a stirred solution of 2,2-dimethyl-3-(4'-hydroxyphenylthio)-propionic acid (1.36 g, 6.0 mmol) and pyridine (1.03 g, 13.0 mmol) in 10 mL of THF under N2. After 6 days, 30 mL of ether was added and the reaction mixture filtered into a separatory funnel. The organic layer was washed with 0.5N HCl (2×15 mL), saturated NaCl (15 mL), 1:9 saturated NaHCO3 /H2O (2×15 mL), saturated NaCl (15 mL) and dried over anhydrous MgSO4. Filtration and evaporation provided 1.96 g (88%) of the desired ester. 1H NMR (CDCl3) δ0.974 (t, 3H, J=7.2 Hz), 1.27 (s, 6H), 1.82-1.96 (m, 1H), 2.13-2.28 (m, 1H), 3.13 (s, 2H), 3.67 (t, 1H, J=7.5 Hz), 6.90 (d, 2H, J=8.7 Hz), 7.30-7.38 (ArH, 7H), 11.9 (br s, --OH); 13C NMR (CDCl3) δ11.84, 24.30, 26.45, 43.73, 44.95, 53.27, 122.06, 127.58, 128.01, 128.88, 131.66, 134.27, 138.58, 149.65, 172.75, 183.22. the reaction mixture filtered into a separatory funnel The organic layer was washed with 0.5N HCl (2×15 mL), saturated NaCl (15 mL), 1:9 saturated NaHCO3 /H2O (2×15 mL), saturated NaCl (15 mL) dried over anhydrous MgSO4 Filtration and evaporation

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

Procedure: A solution of 2-phenylbutyryl chloride (1.19 g, 6.5 mmol) in 5 mL of THF was added to a stirred solution of 2,2-dimethyl-3-(4'-hydroxyphenylthio)-propionic acid (1.36 g, 6.0 mmol) and pyridine (1.03 g, 13.0 mmol) in 10 mL of THF under N2. After 6 days, 30 mL of ether was added and the reaction mixture filtered into a separatory funnel. The organic layer was washed with 0.5N HCl (2×15 mL), saturated NaCl (15 mL), 1:9 saturated NaHCO3 /H2O (2×15 mL), saturated NaCl (15 mL) and dried over anhydrous MgSO4. Filtration and evaporation provided 1.96 g (88%) of the desired ester. 1H NMR (CDCl3) δ0.974 (t, 3H, J=7.2 Hz), 1.27 (s, 6H), 1.82-1.96 (m, 1H), 2.13-2.28 (m, 1H), 3.13 (s, 2H), 3.67 (t, 1H, J=7.5 Hz), 6.90 (d, 2H, J=8.7 Hz), 7.30-7.38 (ArH, 7H), 11.9 (br s, --OH); 13C NMR (CDCl3) δ11.84, 24.30, 26.45, 43.73, 44.95, 53.27, 122.06, 127.58, 128.01, 128.88, 131.66, 134.27, 138.58, 149.65, 172.75, 183.22. the reaction mixture filtered into a separatory funnel The organic layer was washed with 0.5N HCl (2×15 mL), saturated NaCl (15 mL), 1:9 saturated NaHCO3 /H2O (2×15 mL), saturated NaCl (15 mL) dried over anhydrous MgSO4 Filtration and evaporation

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

Procedure: Thionyl chloride (0.12 mol) in 60 mL of CH2Cl2 was added to a stirred solution of 2-phenylbutyric acid (16.4 g, 0.10 mol). A catalytic amount of DMF was added and the reaction was allowed to continue overnight at room temperature. The volatiles were removed under vacuum and the residual liquid was vacuum distilled to yield 12.4 g (68%) of 2-phenylbutyryl chloride. IR (neat) 1798 cm-1 (C=O). The volatiles were removed under vacuum distilled