Hydrochloric Acid → 7-Benzyloxy-2-oxo-2H-chromene-3-carboxylic acid

HRID 272801Notes

Reaction equation

HRID 272801 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:23])[O:7][C:8]2[CH:14]=[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:4].[OH-].[Na+].Cl.O>C(O)C>[CH2:16]([O:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6](=[O:23])[O:7][C:8]=2[CH:14]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 99726517-benzyloxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester

Product 1

HCID 103571927-Benzyloxy-2-oxo-2H-chromene-3-carboxylic acidYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound 1 (0.1 g, 0.32 mmol) is dissolved in ethanol (0.5 mL), and 10% of sodium hydroxide aqueous solution (0.5 mL) is added into. The resulting mixture is reacted for 1 hour with reflux. After cooling, the strong hydrochloric acid (0.3 mL) is added and followed by stirring for 10 minutes. 5 mL of water is added, and produced solid is obtained by filtration. The filter cake is washed with water, followed by drying to obtain 0.09 g of the captioned compound, yield: 90%. m.p. 196-197° C. 1H NMR (DMSO-d6): δ=5.25(s, 2 H), 7.08(dd, J=2.2 Hz, 8.8 Hz, 1H), 7.12(d, J=2.2 Hz, 1H), 7.30-7.50(m, 5H), 7.83(d, J=8.8 Hz, 1H), 8.73(s, 1H); Elements Analysis, C17H12O5 (296): Calculated C, 68.92; H, 4.05; Found C, 68.50; H, 4.12; IR(KBr) : 3054.7, 1747.2, 1677.8, 1600.7, 1556.3, 1421.3, 1378.9, 1257.4, 1209.2, 1120.2, 732.8 cm−1; EI-MS(m/z): 296(4, M+), 91(100).

Workup

  1. customThe resulting mixture is reacted for 1 hour
  2. temperaturewith reflux
  3. temperatureAfter cooling
  4. customproduced solid
  5. customis obtained by filtration
  6. washThe filter cake is washed with water
  7. customby drying

Sources & evidence

ORD record
ord-314cc7e2a0994938913d4ff3ca910fba
Source dataset
uspto-grants-2008_11
Patent number
US07456205B2

Reaction notes

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