Hydrochloric Acid → 2-Hydroxymethylene-5-methoxy-1-indanone

HRID 1816462Notes

Reaction equation

HRID 1816462 reaction equation
C[O-].[Na+].[CH:4](OCC)=[O:5].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14]2.Cl>C1COCC1>[OH:5][CH:4]=[C:15]1[CH2:14][C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH3:9])[CH:12]=2)[C:16]1=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 787875-Methoxyindan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 697542672-Hydroxymethylene-5-methoxy-1-indanoneYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of sodium methoxide (1.2 g, 22 mmol) in THF (20 mL) was added ethyl formate (1.6 g, 22 mmol) and 5-methoxy-1-indanone (3.24 g, 19.7 mmol) and the mixture stirred for 16 h at 23° C. The reaction mixture was added to aqueous HCl (0.1 N) and extracted with a mixture (1:1) of ethyl acetate and ether (2×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated to a residue, which was purified by chromatography (silica, 40% ethyl acetate in hexanes) to give an oil (2.6 g, 69%): 1H NMR (CDCl3) δ 7.81 (d, J=9.6 Hz, 1H), 7.47 (s, 1H), 7.00 (m, 2H), 3.94 (s, 3H), 3.9 (m, 2H); MS m/z 191 [M+H]+.

Workup

  1. extractionextracted with a mixture (1:1) of ethyl acetate and ether (2×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated to a residue, which
  4. customwas purified by chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-355ce6c8f57349cc9043dd7bf90b6595
Source dataset
uspto-grants-2005_04
Patent number
US06884816B2

Reaction notes

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