Formaldehyde → (6-propyl-1,3-benzodioxol-5-yl)methyl acetate

HRID 1034348Notes

Reaction equation

HRID 1034348 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.[C:13]([O:16][C:17](=O)C)(=[O:15])[CH3:14].C=O.S(=O)(=O)(O)O>CCCCCC.C(O)(=O)C.O>[C:13]([O:16][CH2:17][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:15])[CH3:14]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 67302335HCID 67302335, compound

Product 1

HCID 239316(6-propyl-1,3-benzodioxol-5-yl)methyl acetateYield 59%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

Dihydrosafrole (20 g), acetic acid (100 g) and water (10 g) were added to a mixture of acetic acid (250 ml), hexane (200 ml), acetic anhydride (40 g) and paraformaldehyde (40 g) to which 1.7 g of 40% sulphuric acid had been added. The reaction mixture was held at 60° C. for 5 hours and was then cooled to 20° C. and excess paraformaldehyde removed by filtration. Saturated brine (200 ml) was then added followed by ether (100 ml). The mixture was ether extracted (3 times) and combined extracts washed with brine (3 times). Following removal of solvent under reduced pressure the material was distilled under vacuum to give 4,5-methylenedioxy-2-propylbenzyl acetate (8) as a colourless oil (b.pt 154°-165° C. at 2.0 mm Hg) . . . Yield 59%.

Workup

  1. additionhad been added
  2. customexcess paraformaldehyde removed by filtration
  3. additionSaturated brine (200 ml) was then added
  4. extractionextracted (3 times)
  5. washwashed with brine (3 times)
  6. customremoval of solvent under reduced pressure the material
  7. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-922dbb280a5f41dbaf3d5469eb7e6f90
Source dataset
uspto-grants-1994_05
Patent number
US05315018

Reaction notes

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