4-butoxybenzaldehyde

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 mixture of 3.6 g of 2-(4-pentenyl)-1,3-propanediol, 4.4 g of p-butoxybenzaldehyde, 75 ml of toluene and 3 drops of 10% sulphuric acid was heated to boiling for 2.5 hours, whereby about 50 ml of wet solvent were distilled off and were replaced by the dropwise addition of 50 ml of fresh toluene. Thereafter, the mixture was neutralized with 4 drops of triethylamine and, after cooling, was extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time and twice with 50 ml of water each time. The organic phase was dried over sodium sulphate and concentrated. The residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8), whereby 4.2 g of trans-4-(p-butoxyphenyl)-5-(4-pentenyl)-m-dioxane were obtained. Two-fold recrystallization from hexane gave 2.2 g of pure product with m.p. (C-N) 29.5° C. and cl.p. (N-I) 30.7° C. was heated whereby about 50 ml of wet solvent were distilled off were replaced by the dropwise addition of 50 ml of fresh toluene after cooling was extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time The organic phase was dried over sodium sulphate concentrated The residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8)

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

Procedure: A mixture of 3.6 g of 2-(4-pentenyl)-1,3-propanediol, 4.4 g of p-butoxybenzaldehyde, 75 ml of toluene and 3 drops of 10% sulphuric acid was heated to boiling for 2.5 hours, whereby about 50 ml of wet solvent were distilled off and were replaced by the dropwise addition of 50 ml of fresh toluene. Thereafter, the mixture was neutralized with 4 drops of triethylamine and, after cooling, was extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time and twice with 50 ml of water each time. The organic phase was dried over sodium sulphate and concentrated. The residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8), whereby 4.2 g of trans-4-(p-butoxyphenyl)-5-(4-pentenyl)-m-dioxane were obtained. Two-fold recrystallization from hexane gave 2.2 g of pure product with m.p. (C-N) 29.5° C. and cl.p. (N-I) 30.7° C. was heated whereby about 50 ml of wet solvent were distilled off were replaced by the dropwise addition of 50 ml of fresh toluene after cooling was extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time The organic phase was dried over sodium sulphate concentrated The residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8)

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

Procedure: This compound was synthesized from 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) and p-butoxybenzaldehyde (3.56 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.82 g, 73%) as white crystals (mp: 56-57° C.). IR: 3350-2500, 1700 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.50 (m, 2H), 1.80 (m, 4H), 2.40 (m, 4H), 3.90 (t, 2H), 5.50+6.00 (m, 1H), 6.38 (q, 1H), 7.05 (q, 4H), 11.00 (bs, 1H). Anal. Calcd. for C16H22O3 : C, 73.25, H, 8.45%; Found: C, 73.32, H, 8.46%. Z:E=37:63. Crystallization (petroleum ether)

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

Procedure: This compound was synthesized from 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) and p-butoxybenzaldehyde (3.56 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.82 g, 73%) as white crystals (mp: 56-57° C.). IR: 3350-2500, 1700 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.50 (m, 2H), 1.80 (m, 4H), 2.40 (m, 4H), 3.90 (t, 2H), 5.50+6.00 (m, 1H), 6.38 (q, 1H), 7.05 (q, 4H), 11.00 (bs, 1H). Anal. Calcd. for C16H22O3 : C, 73.25, H, 8.45%; Found: C, 73.32, H, 8.46%. Z:E=37:63. Crystallization (petroleum ether)

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

Procedure: The title compound was prepared according to the procedure described in Example 11 using 4-butoxybenzaldehyde and N-tert-butylhydroxylamine. The title compound was isolated in 96% yield (7.18 g) as a solid, m.p. 68.5° C. Spectroscopic data were as follows: The title compound was prepared

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

Procedure: The title compound was prepared according to the procedure described in Example 11 using 4-butoxybenzaldehyde and N-tert-butylhydroxylamine. The title compound was isolated in 96% yield (7.18 g) as a solid, m.p. 68.5° C. Spectroscopic data were as follows: The title compound was prepared