6-(oxan-2-yloxy)hexan-1-ol

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

Procedure: Hexane-1,6-diol (70.9 g) was melted in a water bath at ca. 60°, the melt cooled to 45° and dihydropyran (16.82 g) quickly added followed by 10 N hydrochloric acid (0.1 ml). The mixture was stirred and cold water added to maintain a reaction temperature of approximately 50°. When the exotherm had subsided, the mixture was stirred at room temperature for 0.5 h, then diluted with water (500 ml) and extracted with ER (2×250 ml). The ER solution was washed with water (3×500 ml), dried and concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1) affording the title compound (19.6 g). T.l.c. (EA/hexane 1:1) Rf 0.40. the melt cooled to 45° to maintain a reaction temperature of approximately 50° the mixture was stirred at room temperature for 0.5 h extracted with ER (2×250 ml) The ER solution was washed with water (3×500 ml) dried concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1)

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

Procedure: Hexane-1,6-diol (70.9 g) was melted in a water bath at ca. 60°, the melt cooled to 45° and dihydropyran (16.82 g) quickly added followed by 10 N hydrochloric acid (0.1 ml). The mixture was stirred and cold water added to maintain a reaction temperature of approximately 50°. When the exotherm had subsided, the mixture was stirred at room temperature for 0.5 h, then diluted with water (500 ml) and extracted with ER (2×250 ml). The ER solution was washed with water (3×500 ml), dried and concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1) affording the title compound (19.6 g). T.l.c. (EA/hexane 1:1) Rf 0.40. the melt cooled to 45° to maintain a reaction temperature of approximately 50° the mixture was stirred at room temperature for 0.5 h extracted with ER (2×250 ml) The ER solution was washed with water (3×500 ml) dried concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1)

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

Procedure: Pyridine-sulphur trioxide complex (17.1 g., 0.108 mole) in dimethylsulphoxide (90 ml.) was added dropwise to a mixture of 6-(2-tetrahydropyranyloxy)-hexanol (7.2 g., 0.036 mole) and triethylamine (27 g., 0.27 mole) in dimethylsulphoxide (90 ml.) at 25°C. The mixture was stirred for a further hour, then 2N acetic acid (100 ml.), water (200 ml.) and diethyl ether (500 ml.) added successively, the layers separated and the aqueous layer extracted with diethyl ether. The combined ether solutions were washed quickly with 2N hydrochloric acid, aqueous sodium carbonate and then water, and dried over sodium sulphate. The solvent was evaporated and the residue distilled under reduced pressure to give 6-(2-tetrahydropyranyloxy)hexanal (4.65 g., 63%), b.p. 75°-105°C./0.15 mm.Hg. the layers separated the aqueous layer extracted with diethyl ether The combined ether solutions were washed quickly with 2N hydrochloric acid, aqueous sodium carbonate water, and dried over sodium sulphate The solvent was evaporated the residue distilled under reduced pressure

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

Procedure: 6-(2-Tetrahydropyranyloxy)hexanol was prepared by a modification of the method described by Bohlmann, Jeute and Reinecke, Chem. Ber., 1969, 102, 3283. 3,4-Dihydro-2-H-pyran (33.6 g., 0.4 mole) was added dropwise at 30°C. with stirring to hexane-1,6-diol (47.2 g., 0.4 mole) in chloroform (500 ml.) and concentrated hydrochloric acid (30 drops). The temperature was allowed to rise to 40°C. and maintained at this level for 3 hours. The solution was then washed with aqueous sodium bicarbonate and then water and dried over potassium carbonate. The solvent was removed in vacuo, and the residue distilled under reduced pressure to give 6-(2-tetrahydropyranyloxy)hexanol (46.1 g., 57%), b.p. 102°-120°C./0.2 mm.Hg. 6-(2-Tetrahydropyranyloxy)hexanol was prepared by a modification of the method to rise to 40°C. maintained at this level for 3 hours The solution was then washed with aqueous sodium bicarbonate water and dried over potassium carbonate The solvent was removed in vacuo the residue distilled under reduced pressure

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

Procedure: Hexane-1,6-diol (70.9 g) was melted in a water bath at ca. 60°, the melt cooled to 45° and dihydropyran (16.82 g) quickly added followed by 10 N hydrochloric acid (0.1 ml). The mixture was stirred and cold water added to maintain a reaction temperature of approximately 50°. When the exotherm had subsided, the mixture was stirred at room temperature for 0.5 h, then diluted with water (500 ml) and extracted with ER (2×250 ml). The ER solution was washed with water (3×500 ml), dried and concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1) affording the title compound (19.6 g). T.l.c. (EA/hexane 1:1) Rf 0.40. the melt cooled to 45° to maintain a reaction temperature of approximately 50° the mixture was stirred at room temperature for 0.5 h extracted with ER (2×250 ml) The ER solution was washed with water (3×500 ml) dried concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1)