Methanol → HCID 67403812, compound

HRID 906088Notes

Reaction equation

HRID 906088 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH:13]=C)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][OH:17]>>[CH3:15][C:3]1[C:2]2[O:1][CH:13]([O:17][CH3:16])[CH2:12][C:11]=2[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 887MethanolHCID 67404181HCID 67404181, compound

Product 1

HCID 67403812HCID 67403812, compoundYield 90%

Conditions

Temperature
-78 °C

Procedure

A solution of methyl 3-hydroxy-2-methyl-4-prop-2-en-1-ylbenzoate (1.64 g, 8.0 mmol) in methanol (20 mL) was cooled to −78° C. While maintaining the reaction temperature at −78° C., ozone was bubbled into the reaction mixture for 30 minutes, followed by the addition of dimethyl sulfide (5 mL). The reaction mixture was allowed to warm to room temperature and was then stirred for an additional 15 hours. The reaction mixture was concentrated in vacuo and diluted with diethyl ether. The organic portion was washed with water, brine, dried over sodium sulfate and concentrated to afford (1.59 g, 90%) of methyl 7-methyl-2-(methyloxy)-2,3-dihydro-1-benzofuran-6-carboxylate as a yellow oil. MS (EI) for C12H14O4: 223 (MH+).

Workup

  1. customozone was bubbled into the reaction mixture for 30 minutes
  2. additionfollowed by the addition of dimethyl sulfide (5 mL)
  3. temperatureto warm to room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with diethyl ether
  6. washThe organic portion was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-45f3056455824878bd41ec98dfd7cfee
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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