Acetone → 2,2-Dimethyl-4-oxo-4H-benzo[d][1,3]dioxine-6-carbaldehyde

HRID 551922Notes

Reaction equation

[CH:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1)=[O:2].[CH3:13][C:14]([CH3:16])=O>C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>[CH3:13][C:14]1([CH3:16])[O:12][C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][C:7]=2[C:8](=[O:10])[O:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 5-formylsalicylic acid (Aldrich, 4.12 g, 24.8 mmol) in TFA (30 ml), TFAA (10 ml) and acetone (10 ml) was heated at 90° C. overnight. The reaction mixture was concentrated under reduced pressure. The residual oil was taken up in EtOAc and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried- over MgSO4 and the solvent was removed under reduces pressure. The crude product was purified by flash chromatography on silicagel (EtOAc/c-Hex (80/20)) to give 1.8 g (35%) of the title compound as a white powder. 1H NMR (CDCl3) δ: 1.80 (s, 6H), 7.09 (d, J=8.7 Hz, 1H), 8.09 (dd, J=8.7, 2.3 Hz, 1H), 8.45 (d, J=1.9 Hz, 1H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
washwashed with a saturated aqueous solution of NaHCO3 and brine
customthe solvent was removed
customThe crude product was purified by flash chromatography on silicagel (EtOAc/c-Hex (80/20))

Sources & evidence

ORD record: ord-35f177985f084650acfde925312f30ee
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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