oct-7-ene-1,2-diol

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

Procedure: A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil. extracted with ether The ether solution was dried evaporated The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period was poured into water extracted with ether The ether solution was dried evaporated The residue was dissolved in 400 ml of methanol stirred with 35 g of Amberlyst 15 resin The solution was filtered solvent was removed The residue was purified by chromatography

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

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

Procedure: A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil. extracted with ether The ether solution was dried evaporated The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period was poured into water extracted with ether The ether solution was dried evaporated The residue was dissolved in 400 ml of methanol stirred with 35 g of Amberlyst 15 resin The solution was filtered solvent was removed The residue was purified by chromatography

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

Procedure: A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil. extracted with ether The ether solution was dried evaporated The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period was poured into water extracted with ether The ether solution was dried evaporated The residue was dissolved in 400 ml of methanol stirred with 35 g of Amberlyst 15 resin The solution was filtered solvent was removed The residue was purified by chromatography

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

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

Procedure: A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60% sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil. extracted with ether The ether solution was dried evaporated The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide this solution was added dropwise to a suspension of 17.75 g of 60% sodium hydride in 500 ml of dimethylformamide over a 2 hour period was poured into water extracted with ether The ether solution was dried evaporated The residue was dissolved in 400 ml of methanol stirred with 35 g of Amberlyst 15 resin The solution was filtered solvent was removed The residue was purified by chromatography

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

Procedure: A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60% sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil. extracted with ether The ether solution was dried evaporated The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide this solution was added dropwise to a suspension of 17.75 g of 60% sodium hydride in 500 ml of dimethylformamide over a 2 hour period was poured into water extracted with ether The ether solution was dried evaporated The residue was dissolved in 400 ml of methanol stirred with 35 g of Amberlyst 15 resin The solution was filtered solvent was removed The residue was purified by chromatography

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

Procedure: 198 g (6.6 mol) of sodium hydride (80% strength) and 500 g of toluene are introduced into a flask, and the mixture is heated to the reflux temperature. 432 g (3 mol) of 7-octene-1,2-diol, dissolved in 1,500 g of toluene, are then added over 3 hours, and the mixture is stirred at the reflux temperature until hydrogen evolution is complete. 830 g (6.6 mol) of dimethyl sulphate are added over 4 hours, and the mixture is stirred for a further 2 hours. After addition of 50 ml of methanol, 1,500 g of water are added in order to dissolve the precipitate. The phases are separated and the organic phase is distilled. 420 g of 1,2-dimethoxyoct-7-ene having a boiling point of 80° C./10 mbar, corresponding to a yield of 81% of theory) are obtained. the mixture is heated to the reflux temperature are then added over 3 hours are added in order to dissolve the precipitate The phases are separated the organic phase is distilled