4-hydroxy-3,5-di(propan-2-yl)benzaldehyde

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: Prepared according to the procedure described in Example 92 using 3,5-diisopropyl-4-hydroxybenzaldehyde (2.7 g, 13 mmoles) and 1-methyl hydantoin (1.4 g, 12 mmoles). Recrystallization from acetonitrile gave the pure product (0.4 g), mp 197°-208° C. Prepared Recrystallization from acetonitrile

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

Procedure: Prepared according to the procedure described in Example 92 using 3,5-diisopropyl-4-hydroxybenzaldehyde (2.7 g, 13 mmoles) and 1-methyl hydantoin (1.4 g, 12 mmoles). Recrystallization from acetonitrile gave the pure product (0.4 g), mp 197°-208° C. Prepared Recrystallization from acetonitrile

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

Procedure: Prepared according to the procedure described in Example 1 using 4-hydroxy-3,5-bis(1-methylethyl)benzaldehyde (3.0 g, 15 mmoles), 2-thiohydantoin (1.6 g, 14 mmoles), sodium acetate (4.2 g, 51 mmoles), and acetic acid (35 ml), filtered off, dried, and recrystallized from acetonitrile to afford the pure product (1.4 g), mp 225°-230° C. Prepared filtered off dried recrystallized from acetonitrile

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

Procedure: Prepared according to the procedure described in Example 1 using 4-hydroxy-3,5-bis(1-methylethyl)benzaldehyde (3.0 g, 15 mmoles), 2-thiohydantoin (1.6 g, 14 mmoles), sodium acetate (4.2 g, 51 mmoles), and acetic acid (35 ml), filtered off, dried, and recrystallized from acetonitrile to afford the pure product (1.4 g), mp 225°-230° C. Prepared filtered off dried recrystallized from acetonitrile

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.90 g (6 mmol) of (1-acetyl-2-oxopyrrolidin-3-yl)triphenylphosphonium bromide in ethanol (12 ml) were added 1.24 g (6 mmol) of 3,5-di-isopropyl-4-hydroxybenzaldehyde and 1.67 ml (12 mmol) of triethylamine, and the mixture was stirred with heating at 60° C. for 2 hours. The reaction mixture was evaporated to give a residue, which was added with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over magnesium sulfate and evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=4/1) to give 857 mg of the objective compound in 45% yield. The reaction mixture was evaporated to give a residue, which The ethyl acetate layer was washed with water dried over magnesium sulfate evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=4/1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.90 g (6 mmol) of (1-acetyl-2-oxopyrrolidin-3-yl)triphenylphosphonium bromide in ethanol (12 ml) were added 1.24 g (6 mmol) of 3,5-di-isopropyl-4-hydroxybenzaldehyde and 1.67 ml (12 mmol) of triethylamine, and the mixture was stirred with heating at 60° C. for 2 hours. The reaction mixture was evaporated to give a residue, which was added with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over magnesium sulfate and evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=4/1) to give 857 mg of the objective compound in 45% yield. The reaction mixture was evaporated to give a residue, which The ethyl acetate layer was washed with water dried over magnesium sulfate evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=4/1)

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

Procedure: M44 was prepared with 3,5-diisopropyl-4-hydroxybenzaldehyde and N-3-phenyl-n-propyl cyanomethylsulfonamide under similar conditions as described for M40.

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

Procedure: 18 g of 2,6-di isopropyl phenol and 1.8 g HMTA (hexamethylene tetraamine) in 60 ml TFA (trifluoro acetic acid) was refluxed 3.5 hours. Workup, chromatography on silica gel (CH2Cl2) and trituration with hexane gave 5.3 g, 26% yield, white solid, mp-103° C. (3,5,-di-iso-propyl 4 hydroxybenzaldehyde). NMR CDCl3 δ 9.87(1H,S,CHO), 7.63(2H,S), 3.19(2H,septet,J=7.7 Hz), 1.30(12H,d,J=7.7 Hz).