(2,6-dimethylphenyl)methanol

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:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,6-dimethylbenzyl alcohol (17.1 g) and acetic anhydride (14.2 ml) was stirred at 70° C. for 5 hours during which time to the mixture was added 4-dimethylaminopyridine (17 mg). After cooling, the reaction mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate, and the solution was washed with water twice. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give 2,6-dimethylbenzyl acetate (22.50 g) as colorless oil. After cooling the reaction mixture was evaporated in vacuo The residue was dissolved in ethyl acetate the solution was washed with water twice The organic layer was dried over magnesium sulfate evaporated in vacuo

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

Procedure: 17 g of 2,6-dimethyl benzoic acid ethyl ester (0.095 mole) dissolved in 50 ml of ethyl ether are added dropwise as a function of the vigor of reflux to a suspension of 3.72 g (0.095 mole) of LiAlH4 in 100 ml of ether. When the addition is complete, the mixture is heated at reflux for 2h and left to stand overnight. Excess hydride is decomposed by the gradual addition of water (while cooling the flask in an ice-water bath), then 10% HCl. After the usual work-up, the product is crystallized from petroleum ether. 10 g of product are obtained. M.p.=84°. Yield 77.5%. are added dropwise as a function of the vigor When the addition the mixture is heated left After the usual work-up, the product is crystallized from petroleum ether

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

Procedure: A solution of 3-(3-hydroxyphenyl)propanenitrile (Step B, 1.25 g, 8.5 mmol) and diisopropyl azodicarboxylate (DIAD, 1.87 g, 9.26 mmol) in dry THF (10 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (1.27 g, 9.3 mmol) and triphenylphosphine (TPP, 2.43 g, 9.26 mmol) in dry THF (30 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

Procedure: A solution of Ethyl 3-hydroxy-4-methoxybenzoate (Step A, 9.10 g, 46.4 mmol) and diisopropyl azodicarboxylate (DIAD, 10.23 g, 50 mmol) in dry THF (20 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (6.94 g, 51 mmol) and triphenylphosphine (TPP, 13.27 g, 50 mmol) in dry THF (60 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

Procedure: A solution of 2-(3-Hydroxyphenyl)acetonitrile (Step A, 5 g, 37 mmol) and diisopropyl azodicarboxylate (DIAD, 3.38 g, 16.7 mmol) in dry THF (20 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (2.25 g, 16.5 mmol) and triphenylphosphine (TPP, 4.3 g, 16.4 mmol) in THF (30 ml) at 0° C. under argon. The reaction mixture was stirred at room temperature for 16 hours or until all the starting material is consumed. Silica gel (25 g) was added to the mixture, solvents were removed under reduced pressure, loaded on silica gel column and eluted with methylene chloride:hexane (1:1) to give light yellow crystalline solid. is consumed Silica gel (25 g) was added to the mixture, solvents were removed under reduced pressure eluted with methylene chloride:hexane (1:1) to give light yellow crystalline solid