3-chloro-5-hydroxypentan-2-one

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

Procedure: 13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2 mmHG; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J. Am. Chem. Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg. After cooling the reaction mixture was filtered the filtrate evaporated to dryness the residue dissolved in water The aqueous solution was extracted five times with chloroform the combined extracts washed dried evaporated Distillation of the residue

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

Procedure: 13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2 mmHG; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J. Am. Chem. Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg. After cooling the reaction mixture was filtered the filtrate evaporated to dryness the residue dissolved in water The aqueous solution was extracted five times with chloroform the combined extracts washed dried evaporated Distillation of the residue

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

Procedure: 13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2 mmHG; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J. Am. Chem. Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg. After cooling the reaction mixture was filtered the filtrate evaporated to dryness the residue dissolved in water The aqueous solution was extracted five times with chloroform the combined extracts washed dried evaporated Distillation of the residue

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

Procedure: 13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2mmHg; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J.Am.Chem.Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg. After cooling the reaction mixture was filtered the filtrate evaporated to dryness the residue dissolved in water The aqueous solution was extracted five times with chloroform the combined extracts washed dried evaporated Distillation of the residue

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

Procedure: 13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2 mmHG; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J. Am. Chem. Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg. After cooling the reaction mixture was filtered the filtrate evaporated to dryness the residue dissolved in water The aqueous solution was extracted five times with chloroform the combined extracts washed dried evaporated Distillation of the residue