3-methylpentane-1,5-diol

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

Procedure: According to the prior art methods, production of β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol requires respective independent production facilities. On the contrary, the simultaneous production method can produce β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol simultaneously from 2-hydroxy-4-methyltetrahydropyran with a common reactor and under relatively mild conditions. According to this simultaneous production method, β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol are produced generally in a β-methyl-δ-valerolactone/3-methylpentane-1,5-diol mole ratio of about 70/30 to 15/85. Said simultaneous production on method can give β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol each in a satisfactory yield and in a yield ratio therebetween selected depending on the demands therefor.

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

Procedure: According to the prior art methods, production of β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol requires respective independent production facilities. On the contrary, the simultaneous production method can produce β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol simultaneously from 2-hydroxy-4-methyltetrahydropyran with a common reactor and under relatively mild conditions. According to this simultaneous production method, β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol are produced generally in a β-methyl-δ-valerolactone/3-methylpentane-1,5-diol mole ratio of about 70/30 to 15/85. Said simultaneous production on method can give β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol each in a satisfactory yield and in a yield ratio therebetween selected depending on the demands therefor.

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

Procedure: According to the prior art methods, production of β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol requires respective independent production facilities. On the contrary, the simultaneous production method can produce β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol simultaneously from 2-hydroxy-4-methyltetrahydropyran with a common reactor and under relatively mild conditions. According to this simultaneous production method, β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol are produced generally in a β-methyl-δ-valerolactone/3-methylpentane-1,5-diol mole ratio of about 70/30 to 15/85. Said simultaneous production on method can give β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol each in a satisfactory yield and in a yield ratio therebetween selected depending on the demands therefor.

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 25 parts of 3-methyl-1,5-pentanediol, 12 parts of N-methylpyrrolidone, 2.6 parts of phenol and 3.3 parts of potassium carbonate is mixed with 8 parts of 1-amino-4-hydroxy-2-chloroanthraquinone at 130°C and stirred for 3 hours at 130°C and 2 hours at 140°C under nitrogen. After working up, 6 parts of 1-amino-2-(5'-hydroxy-3'-methylpentoxy)-4-hydroxyanthraquinone melting at from 134° to 135°C are obtained.

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

Procedure: 12.5 parts of 1-amino-2-phenoxy-4-hydroxyanthraquinone, 13 parts of 3-methyl-1,5-pentanediol, 25 parts of N-methylpyrrolidone, 3 parts of polyethylene oxide of average molecular weight 300 and 2 parts of anhydrous potassium carbonate are stirred for one hour at 150°C under nitrogen. After working up, 10.5 parts of 1-amino-2-(3'-methyl-5'-hydroxypentanoxy)-4-hydroxyanthraquinone are obtained.

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

Procedure: 12.5 parts of 1-amino-2-phenoxy-4-hydroxyanthraquinone, 13 parts of 3-methyl-1,5-pentanediol, 25 parts of N-methylpyrrolidone, 3 parts of polyethylene oxide of average molecular weight 300 and 2 parts of anhydrous potassium carbonate are stirred for one hour at 150°C under nitrogen. After working up, 10.5 parts of 1-amino-2-(3'-methyl-5'-hydroxypentanoxy)-4-hydroxyanthraquinone are obtained.

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

Procedure: 118 g (1.0 mol) of 3-methyl-1,5-pentanediol and 317 g (1.3 mol) of 1,6-di-bromohexane in 2.5 l of dioxan were treated at room temperature with 28 g (1.1 mol) of 95 percent sodium hydride and subsequently heated under reflux for 24 h. After cooling the reaction mixture was treated with 400 ml of water, neutralized with saturated ammonium chloride solution and subsequently extracted three times with 1 l of tert-butyl methyl ether each time. The combined organic extracts were washed with saturated ammonium chloride solution, dried over magnesium sulphate and concentrated on a rotary evaporator. Starting material and byproducts were removed by distillation in a vacuum at 150° C. bath temperature and 0.09 mbar. As the distillation residue there were obtained 183 g of 66 percent 12-bromo-3-methyl-6-oxadodecan-1-ol (43%), which is sufficiently pure for the further reactions. subsequently heated under reflux for 24 h After cooling the reaction mixture subsequently extracted three times with 1 l of tert-butyl methyl ether each time The combined organic extracts were washed with saturated ammonium chloride solution dried over magnesium sulphate concentrated on a rotary evaporator Starting material and byproducts were removed by distillation in a vacuum at 150° C. bath temperature and 0.09 mbar

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

Procedure: To 3.54 g (30 mmol) of 3-methyl-1,5-pentanediol in 30 ml of dry tetrahydrofuran (THF) at 0° was added 19.2 ml (30 mmol) of 1.56 M n-butyllithium. After 30 min, 3.74 g (30 mmol) of β-methoxyethoxymethyl chloride was added and the reaction was stirred overnight. The reaction was poured into ether and water. The aqueous phase was back-extracted twice with ether. Combined ether layers were washed with sat. NaCl solution and were dried over calcium sulfate. The crude product was placed on 1 m×20 cm prep. SiO2 plates which were then developed with 40% ethyl acetate/hexane. Removal of the second least polar band gave the monoether derivative of 3-methyl-1,5-pentanediol (II). The aqueous phase was back-extracted twice with ether Combined ether layers were washed with sat. NaCl solution were dried over calcium sulfate Removal of the second least polar band

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

Procedure: To 3.54 g (30 mmol) of 3-methyl-1,5-pentanediol in 30 ml of dry tetrahydrofuran (THF) at 0° was added 19.2 ml (30 mmol) of 1.56 M n-butyllithium. After 30 min, 3.74 g (30 mmol) of β-methoxyethoxymethyl chloride was added and the reaction was stirred overnight. The reaction was poured into ether and water. The aqueous phase was back-extracted twice with ether. Combined ether layers were washed with sat. NaCl solution and were dried over calcium sulfate. The crude product was placed on 1 m×20 cm prep. SiO2 plates which were then developed with 40% ethyl acetate/hexane. Removal of the second least polar band gave the monoether derivative of 3-methyl-1,5-pentanediol (II). The aqueous phase was back-extracted twice with ether Combined ether layers were washed with sat. NaCl solution were dried over calcium sulfate Removal of the second least polar band

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

Procedure: To 3.54 g (30 mmol) of 3-methyl-1,5-pentanediol in 30 ml of dry tetrahydrofuran (THF) at 0° was added 19.2 ml (30 mmol) of 1.56 M n-butyllithium. After 30 min, 3.74 g (30 mmol) of β-methoxyethoxymethyl chloride was added and the reaction was stirred overnight. The reaction was poured into ether and water. The aqueous phase was back-extracted twice with ether. Combined ether layers were washed with sat. NaCl solution and were dried over calcium sulfate. The crude product was placed on 1 m×20 cm prep. SiO2 plates which were then developed with 40% ethyl acetate/hexane. Removal of the second least polar band gave the monoether derivative of 3-methyl-1,5-pentanediol (II). The aqueous phase was back-extracted twice with ether Combined ether layers were washed with sat. NaCl solution were dried over calcium sulfate Removal of the second least polar band

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

Procedure: According to the prior art methods, production of β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol requires respective independent production facilities. On the contrary, the simultaneous production method can produce β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol simultaneously from 2-hydroxy-4-methyltetrahydropyran with a common reactor and under relatively mild conditions. According to this simultaneous production method, β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol are produced generally in a β-methyl-δ-valerolactone/3-methylpentane-1,5-diol mole ratio of about 70/30 to 15/85. Said simultaneous production on method can give β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol each in a satisfactory yield and in a yield ratio therebetween selected depending on the demands therefor.

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

Procedure: According to the prior art methods, production of β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol requires respective independent production facilities. On the contrary, the simultaneous production method can produce β-methyl-δ-valerolactone and 3-methylpentane-1,5-diol simultaneously from 2-hydroxy-4-methyltetrahydropyran with a common reactor and under relatively mild conditions. According to this simultaneous production method, β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol are produced generally in a β-methyl-δ-valerolactone/3-methylpentane-1,5-diol mole ratio of about 70/30 to 15/85. Said simultaneous production on method can give β-methyl-δ-valerolactone and 3-methylpentane- 1,5-diol each in a satisfactory yield and in a yield ratio therebetween selected depending on the demands therefor.