Acetic Acid → (6-propyl-1,3-benzodioxol-5-yl)methyl acetate
Reaction equation
[O:1]1[C:12]2[CH:4]([CH2:5][C:6](=[CH:10][CH:11]=2)[CH2:7][CH:8]=[CH2:9])[O:3][CH2:2]1.[CH2:13]=O.S(=O)(=O)(O)O.CO.[C:22]([OH:25])(=[O:24])[CH3:23]>>[C:22]([O:25][CH2:13][C:10]1[CH:11]=[C:12]2[O:1][CH2:2][O:3][C:4]2=[CH:5][C:6]=1[CH2:7][CH2:8][CH3:9])(=[O:24])[CH3:23]Participants
Procedure
A mixture of dihydrosafrole, 25 g, in acetic acid (25 g) was added, with stirring over 3 hours to a mixture of acetic acid (230 g), paraformaldehyde (45 g) and sulphuric acid (10%, 1.6 g) held at 70° C. After the reaction had been shown to be complete by glc, the excess paraformaldehyde was removed by filtration and the filtrate poured into water (450 ml). Sodium hydroxide solution (20 ml of a 10% solution) was then added. Ether extraction, followed by drying over magnesium sulphate, filtration and evaporation of solvent gave an oil. Methanol (30 ml) was added and after cooling to 0° C. a colourless precipitate of "dimer" (7) was removed by filtration. Evaporation of the filtrate gave 12.7 g of an oil which was purified by distillation to give 7.3 g of colourless oil as 4,5-methylenedioxy-2-propylbenzyl acetate. (b.p. 176°-185° C. at 0.4 mmHg).
Workup
- customheld at 70° C
- customthe excess paraformaldehyde was removed by filtration
- additionthe filtrate poured into water (450 ml)
- additionSodium hydroxide solution (20 ml of a 10% solution) was then added
- extractionEther extraction
- dry with materialby drying over magnesium sulphate, filtration and evaporation of solvent
- customgave an oil
- customwas removed by filtration
- customEvaporation of the filtrate
Sources & evidence
- ORD record
- ord-bd3fc655f0a64adfbd80067ed8cb31da
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05315018
Reaction notes
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