ethyl 4-hydroxy-3,5-dimethylbenzoate

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

Procedure: A mixture of 500 mg (3 mmol) of 4-hydroxy-3,5-dimethylbenzoic acid, 20 ml of absolute ethanol and a catalytic amount of anhydrous HCl was heated at reflux for 2 h. The mixture was then poured into excess cold water and the resultant precipitate was filtered. The precipitate was washed with water and dried in-vacuo to give the title compound as a white solid. at reflux for 2 h the resultant precipitate was filtered The precipitate was washed with water dried in-vacuo

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

Procedure: A mixture of 500 mg (3 mmol) of 4-hydroxy-3,5-dimethylbenzoic acid, 20 ml of absolute ethanol and a catalytic amount of anhydrous HCl was heated at reflux for 2 h. The mixture was then poured into excess cold water and the resultant precipitate was filtered. The precipitate was washed with water and dried in-vacuo to give the title compound as a white solid. at reflux for 2 h the resultant precipitate was filtered The precipitate was washed with water dried in-vacuo

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

Procedure: Ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-3,5-dimethylbenzoate-Using ethyl 4-hydroxy-3,5-dimethylbenzoate, the title compound was synthesized as a white solid. PMR (CDCl3): δ 1.37 (6H, s), 1.39 (6H, s), 1.44 (3H, t, J~7.0 Hz), 1.77 (4H, s), 2.27 (6H, s), 4.41 (2H, q, J~7.0 Hz), 7.50 (1H, d, J~8.4 Hz), 7.86 (2H, s), 8.03 (1H, dd, J~8.4 Hz, 2.0 Hz), 8.23 (1H, d, J~2.0 Hz).

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

Procedure: Ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-3,5-dimethylbenzoate-Using ethyl 4-hydroxy-3,5-dimethylbenzoate, the title compound was synthesized as a white solid. PMR (CDCl3): δ 1.37 (6H, s), 1.39 (6H, s), 1.44 (3H, t, J~7.0 Hz), 1.77 (4H, s), 2.27 (6H, s), 4.41 (2H, q, J~7.0 Hz), 7.50 (1H, d, J~8.4 Hz), 7.86 (2H, s), 8.03 (1H, dd, J~8.4 Hz, 2.0 Hz), 8.23 (1H, d, J~2.0 Hz).

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

Procedure: A suspension of 6.42 g ethyl 3,5-dimethyl-4-hydroxybenzoate, 5.5 g potassium iodide, 3.7 g 1-chloro-4-pentyne and 2.3 g powdered potassium hydroxide in 650 ml acetonitrile was heated at reflux under nitrogen for 16 hrs. The mixture was filtered, concentrated in vacuo and subjected to flash filtration (silica gel, 4:1 hexane/ethyl acetate) to give 7.4 g ethyl 3,5-dimethyl-4-(3-ethynylpropoxy)benzoate as a yellow oil. was heated at reflux under nitrogen for 16 hrs The mixture was filtered concentrated in vacuo subjected to flash filtration (silica gel, 4:1 hexane/ethyl acetate)

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

Procedure: A mixture of 500 mg (3 mmol) of 4-hydroxy-3,5-dimethylbenzoic acid, 20 ml of absolute ethanol and a catalytic amount of anhydrous HCl was heated at reflux for 2 h. The mixture was then poured into excess cold water and the resultant precipitate was filtered. The precipitate was washed with water and dried in-vacuo to give the title compound as a white solid. at reflux for 2 h the resultant precipitate was filtered The precipitate was washed with water dried in-vacuo

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

Procedure: Ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-3,5-dimethylbenzoate-Using ethyl 4-hydroxy-3,5-dimethylbenzoate, the title compound was synthesized as a white solid. PMR (CDCl3): δ 1.37 (6H, s), 1.39 (6H, s), 1.44 (3H, t, J~7.0 Hz), 1.77 (4H, s), 2.27 (6H, s), 4.41 (2H, q, J~7.0 Hz), 7.50 (1H, d, J~8.4 Hz), 7.86 (2H, s), 8.03 (1H, dd, J~8.4 Hz, 2.0 Hz), 8.23 (1H, d, J~2.0 Hz).