Piperonyl alcohol synthesis
- Product Name:Piperonyl alcohol
- CAS Number:495-76-1
- Molecular formula:C8H8O3
- Molecular Weight:152.15
Yield:495-76-1 89%
Reaction Conditions:
Stage #1:piperonal with diisobutylaluminium hydride in dichloromethane at -78; for 1.5 h;
Stage #2:methanol at 20;
Steps:
1.1 Example [1.]; Synthesis [OF 4-R (2-PROPYLSULFANYL) METHYLL-1,] 2-benzenediol; (Step 1) Preparation of 1, 3-benzodioxol-5-yl-methanol
After piperonal [(5G)] was dissolved in dichloromethane (340mL), 1M of DIBAL solution (200mL) was added in the resulting mixture [AT-78°C] and then stirred [AT-78°C] for 90 minutes. Then, methyl alcohol [(LOML)] was added in the resulting mixture, and the temperature of the resulting mixture was raised to room temperature. The resulting solution was diluted with diethylether (250mL) and washed with salt water [(50ML).] The organic layer was dried with anhydrous magnesium sulfate to remove solvent. A column chromatography was performed using ethyl acetate: n-hexane (1 [3)] as an eluent to obtain the compound of Formula 2 (10.92g) (Rf: 0.24, yield: 89%). The compound was dissolved in [CDCL3] and TMS and then 1H NMR was measured. The result was as follows: 'H [NMR 6] : 4. [578] (s, 2H), 5.95 (s, 2H), 6.79 [(M,] 3H).
References:
REX BIOSCIENCES INC.;Choi, Won, Chul;Suh, Hongsuk;Choi, Jae, Sue;Kim, Dae-Duk;Song, Yeong-Ok WO2004/18416, 2004, A1 Location in patent:Page 10-11
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