Sodium Bicarbonate → 3-Allyloxycatechol

HRID 218265Notes

Reaction equation

HRID 218265 reaction equation
[CH2:1]([O:4][C:5]1[C:13]2[O:12]C(OCC)[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:13]=1[OH:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 699337744-Allyloxy-2-ethoxy-1,3-benzodioxolane

Product 1

HCID 122088813-Allyloxycatechol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 38 (3.3 g, 15 mmol) and p-toluenesulfonic acid monohydrate (0.17 g, 0.9 mmol) in aqueous MeOH (21 mL, MeOH: H2O 20:1) was stirred at rt for 16 h, then neutralised by the addition of saturated NaHCO3 aq. and the methanol was removed in vacuo. The residue was extracted with t-BuOMe (3×) and the organic phase was dried (Na2SO4) and evaporated to dryness to give 39 compound (2.4 g, 95%) which was used as such in the next step:

Workup

  1. customthe methanol was removed in vacuo
  2. extractionThe residue was extracted with t-BuOMe (3×)
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1d246614781d4ec18ae5839655e81a5a
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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