3-hydroxy-4-methylbenzaldehyde

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

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

Procedure: p-methoxybenzaldehyde; 2-hydroxy-p-tolualdehyde; 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and 4-hydroxy-m-tolualdehyde.

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

Procedure: 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and

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

Procedure: 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and

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

Procedure: The title compound was prepared by reaction of commercially available 3-hydroxy-4-methyl-benzaldehyde with ethyl iodide in DMF using K2CO3 as base in analogy to the procedure described in M. J. Ashton, D. C. Cook, G. Fenton, J.-A. Karlsson, M. N. Palfreyman, D. Raeburn, A. J. Ratcliffe, J. E. Souness, S. Thurairatnam and N. Vicker J. Med. Chem. 1994, 37, 1696-1703.

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

Procedure: The title compound was prepared by reaction of commercially available 3-hydroxy-4-methyl-benzaldehyde with ethyl iodide in DMF using K2CO3 as base in analogy to the procedure described in M. J. Ashton, D. C. Cook, G. Fenton, J.-A. Karlsson, M. N. Palfreyman, D. Raeburn, A. J. Ratcliffe, J. E. Souness, S. Thurairatnam and N. Vicker J. Med. Chem. 1994, 37, 1696-1703.

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

Procedure: The title compound was prepared by reaction of commercially available 3-hydroxy-4-methyl-benzaldehyde with ethyl iodide in DMF using K2CO3 as base in analogy to the procedure described in M. J. Ashton, D. C. Cook, G. Fenton, J.-A. Karlsson, M. N. Palfreyman, D. Raeburn, A. J. Ratcliffe, J. E. Souness, S. Thurairatnam and N. Vicker J. Med. Chem. 1994, 37, 1696-1703.

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

Procedure: To a solution of 3-hydroxy-4-methylbenzoic acid (15.22 g, 0.1 mole) in THF (250 mL) was added borane.dimethylsulfide (32.0 mL of a 10.0M solution, 0.32 mole) dropwise. Upon completion of addition, the reaction was stirred for 18 hrs. It was then quenched dropwise by the slow addition of aqueous 10% HCl (250 mL) and extracted with ethylacetate (3×250 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was taken up in CH2Cl2 (500 mL) and pyridinium dichromate (45.15 g, 0.12 mole) was added. The resulting mixture was stirred for 48 hrs. It was then filtered through Celite and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 30:70) to afford 4.55 g of 3-hydroxy-4-methylbenzaldehyde as a yellow solid. Upon completion of addition It was then quenched dropwise by the slow addition of aqueous 10% HCl (250 mL) extracted with ethylacetate (3×250 mL) dried with MgSO4 concentrated The resulting mixture was stirred for 48 hrs It was then filtered through Celite concentrated The resulting residue was chromatographed (silica gel, ether:hexanes, 30:70)

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

Procedure: The title compound was prepared by reaction of commercially available 3-hydroxy-4-methyl-benzaldehyde with ethyl iodide in DMF using K2CO3 as base in analogy to the procedure described in M. J. Ashton, D. C. Cook, G. Fenton, J.-A. Karlsson, M. N. Palfreyman, D. Raeburn, A. J. Ratcliffe, J. E. Souness, S. Thurairatnam and N. Vicker J. Med. Chem. 1994, 37, 1696-1703.

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

Procedure: p-methoxybenzaldehyde; 2-hydroxy-p-tolualdehyde; 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and 4-hydroxy-m-tolualdehyde.

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

Procedure: 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and

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

Procedure: 4-hydroxy-o-tolualdehyde; 6-hydroxy-m-tolualdehyde; and