Hydrochloric Acid → HCID 20745900, compound

Participants

Reaction Conditions

Reaction Steps

2.7 g (10 mmol) [3-[(6-chlorohexyl)oxy]-5-[hydroxymethyl]phenyl] methanol (Example 6) were added to a solution of 2.6 g (12.5 mmol) (E)-4-hydroxy-3-methoxycinnamic acid methyl ester (Example 1) and 3.38 g (12.5 mmol) triphenylphosphine in 40 ml tetrahydrofuran. The colourless solution was cooled to 0° C. and then 5.2 ml (12.5 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise over a period of 2 hours. The mixture was allowed to react for 2 hours at 0° C. and then for 15 hours at room temperature. The reaction mixture was poured into an ice cold 1 M solution of HCl. The aqueous phase was extracted three times with a mixture of tert-butyl-methylether/ethyl acetate. The organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water, dried over magnesium sulfate, filtered and concentrated in vacuum. Purification of the residue by column chromatography on silica gel using hexane:ethyl acetate (1:1) as eluent yielded 2.2 g (48%) of (E)-3-[4-[3-[(6-chlorohexyl)oxy]-5-[hydroxymethyl]benzyloxy]-3-methoxyphenyl]acrylic acid methyl ester as an oily product that solidified on standing.

Provenance & Evidence