1-[2-(hydroxymethyl)phenyl]ethanol

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated

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

Procedure: 1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canonne et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound. to react for 1 h The mixture was partitioned between EA The combined organic extracts were dried over sodium sulfate filtered evaporated to dryness in vacuo The residue was purified by silica gel chromatography with HEP

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated

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

Procedure: 1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canorme et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound. to react for 1 h The mixture was partitioned between EA The combined organic extracts were dried over sodium sulfate filtered evaporated to dryness in vacuo The residue was purified by silica gel chromatography with HEP

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

Procedure: 1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canorme et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound. to react for 1 h The mixture was partitioned between EA The combined organic extracts were dried over sodium sulfate filtered evaporated to dryness in vacuo The residue was purified by silica gel chromatography with HEP

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated

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

Procedure: 1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canonne et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound. to react for 1 h The mixture was partitioned between EA The combined organic extracts were dried over sodium sulfate filtered evaporated to dryness in vacuo The residue was purified by silica gel chromatography with HEP

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

Procedure: Similarly prepared from phthalic anhydride and methylmalonic acid were 2-(1'-oxopropyl)benzoic acid and thence 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene (both as oils). (b) (i) 1-Hydroxymethyl-2-(1'-hydroxyethyl)benzene (10 g) was dissolved in dichloromethane (200 ml) and was saturated with hydrogen bromide gas. The solution was stirred for 2 hr. and volatile materials were evaporated to give 1-hydroxymethyl-2-(1'-bromoethyl)-benzene as an oil. Thionyl chloride (30 ml) was added to the oil and the solution was stirred for 1 hr; evaporation of thionyl chloride gave 1-chloromethyl-2-(1'-bromoethyl)benzene which was used immediately. (ii) Similarly prepared from 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene were 1-hydroxymethyl-2-(1'-bromopropyl)benzene and thence 1-chloromethyl-2-(1'-bromopropyl)benzene (both as oils). and volatile materials were evaporated

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated

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

Procedure: 1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canonne et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound. to react for 1 h The mixture was partitioned between EA The combined organic extracts were dried over sodium sulfate filtered evaporated to dryness in vacuo The residue was purified by silica gel chromatography with HEP

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

Procedure: To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid. was added dropwise After heating under reflux for 6 hours the mixture was cooled The solution was filtered the filtrate was dried over magnesium sulphate filtered evaporated