4-methylpent-2-enoic acid

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

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methyl-2-pentenoic acid (24.0 g, 210 mmol; commercially available from TCI America) in acetone (300 mL) was added K2CO3 (55.8 g, 404 mmol) and the reaction was stirred at 25° C. for 30 min. A solution of benzyl bromide (25.2 mL, 212 mmol; commercially available from Sigma Aldrich) in acetone (100 mL) was then added drop-wise. The reaction mixture was subsequently heated to reflux for 16 hrs. After cooling to 25° C., the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added and the organic layer was separated, washed with brine and dried over Na2SO4. After concentration, the crude product was subjected to silica gel chromatography (1-5% Ether/Hex) to afford 4-methyl-pent-2-enoic acid benzyl ester (40.5 g, 98%): H-NMR (CDCI3) δ 7.36-7.28 (m, 5 H), 6.96 (dd, 1 H), 5.79 (d, 1 H), 5.14 (s, 2 H), 2.45-2.40 (m, 1 H), 1.01 (d, 6 H). The reaction mixture was subsequently heated to reflux for 16 hrs After cooling to 25° C. the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added the organic layer was separated washed with brine dried over Na2SO4 After concentration

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methyl-2-pentenoic acid (24.0 g, 210 mmol; commercially available from TCI America) in acetone (300 mL) was added K2CO3 (55.8 g, 404 mmol) and the reaction was stirred at 25° C. for 30 min. A solution of benzyl bromide (25.2 mL, 212 mmol; commercially available from Sigma Aldrich) in acetone (100 mL) was then added drop-wise. The reaction mixture was subsequently heated to reflux for 16 hrs. After cooling to 25° C., the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added and the organic layer was separated, washed with brine and dried over Na2SO4. After concentration, the crude product was subjected to silica gel chromatography (1-5% Ether/Hex) to afford 4-methyl-pent-2-enoic acid benzyl ester (40.5 g, 98%): H-NMR (CDCI3) δ 7.36-7.28 (m, 5 H), 6.96 (dd, 1 H), 5.79 (d, 1 H), 5.14 (s, 2 H), 2.45-2.40 (m, 1 H), 1.01 (d, 6 H). The reaction mixture was subsequently heated to reflux for 16 hrs After cooling to 25° C. the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added the organic layer was separated washed with brine dried over Na2SO4 After concentration

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methyl-2-pentenoic acid (24.0 g, 210 mmol; commercially available from TCI America) in acetone (300 mL) was added K2CO3 (55.8 g, 404 mmol) and the reaction was stirred at 25° C. for 30 min. A solution of benzyl bromide (25.2 mL, 212 mmol; commercially available from Sigma Aldrich) in acetone (100 mL) was then added drop-wise. The reaction mixture was subsequently heated to reflux for 16 hrs. After cooling to 25° C., the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added and the organic layer was separated, washed with brine and dried over Na2SO4. After concentration, the crude product was subjected to silica gel chromatography (1-5% Ether/Hex) to afford 4-methyl-pent-2-enoic acid benzyl ester (40.5 g, 98%): H-NMR (CDCI3) δ 7.36-7.28 (m, 5 H), 6.96 (dd, 1 H), 5.79 (d, 1 H), 5.14 (s, 2 H), 2.45-2.40 (m, 1 H), 1.01 (d, 6 H). The reaction mixture was subsequently heated to reflux for 16 hrs After cooling to 25° C. the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added the organic layer was separated washed with brine dried over Na2SO4 After concentration

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 70 g (0.61 mol) of trans-4-methyl-2-pentenoic acid and 49 g (0.72 mol) of 1,3-pentadiene was heated for 12 hours at approx. 200° C. in an autoclave. After the reaction mixture had cooled, it was checked by means of GLC for the presence of 4-methyl-2-pentenoic acid. A further 25 g (0.36 mol) of 1,3-pentadiene were added, after which the mixture was again heated for 12 hours at 200° C. This procedure was repeated until no further decrease in the content of 4-methyl-2-pentenoic acid was any longer observed. The reaction mixture obtained was dissolved in 300 ml of ether and extracted with 300 ml of 10% NaOH solution. The alkaline solution thus obtained was acidified with 40 g of concentrated sulphuric acid and then extracted three times with ether. The ether extract was washed with water, dried on MgSO4, evaporated down and distilled. 73 g of 6-isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid were obtained, b.p.: 95°-100° C./70 Pa. After the reaction mixture had cooled after which the mixture was again heated for 12 hours at 200° C The reaction mixture obtained extracted with 300 ml of 10% NaOH solution The alkaline solution thus obtained extracted three times with ether The ether extract was washed with water dried on MgSO4 evaporated down distilled

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methyl-pent-2-enoic acid and 1,2,3,4-tetrahydro-naphthalen-1-ylamine. MS (M+H, 244.2). Prepared in a similar manner

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methyl-2-pentenoic acid (24.0 g, 210 mmol; commercially available from TCI America) in acetone (300 mL) was added K2CO3 (55.8 g, 404 mmol) and the reaction was stirred at 25° C. for 30 min. A solution of benzyl bromide (25.2 mL, 212 mmol; commercially available from Sigma Aldrich) in acetone (100 mL) was then added drop-wise. The reaction mixture was subsequently heated to reflux for 16 hrs. After cooling to 25° C., the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added and the organic layer was separated, washed with brine and dried over Na2SO4. After concentration, the crude product was subjected to silica gel chromatography (1-5% Ether/Hex) to afford 4-methyl-pent-2-enoic acid benzyl ester (40.5 g, 98%): H-NMR (CDCI3) δ 7.36-7.28 (m, 5 H), 6.96 (dd, 1 H), 5.79 (d, 1 H), 5.14 (s, 2 H), 2.45-2.40 (m, 1 H), 1.01 (d, 6 H). The reaction mixture was subsequently heated to reflux for 16 hrs After cooling to 25° C. the acetone was removed under reduced pressure and ether (300 mL) and water (300 mL) were added the organic layer was separated washed with brine dried over Na2SO4 After concentration