Sodium Hydroxide → HCID 25140790, compound

HRID 560283Notes

Reaction equation

HRID 560283 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]2[CH:9]=[CH:10][CH2:11][O:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:6]>CO.O>[O:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:7]([C:5]([OH:6])=[O:4])[C:8]=2[CH:9]=[CH:10][CH2:11]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57437183HCID 57437183, compound

Product 1

HCID 25140790HCID 25140790, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of NaOH (7.26 mmol) in a mixture of MeOH (5.4 mL) and water (12.1 mL) is added to 2H-chromene-5-carboxylic acid methyl ester (4.84 mmol). The mixture is stirred at 55° C. for 3 h, partially concentrated in vacuo to remove MeOH and made acidic by addition of aq. HCl (1.0M). The desired carboxylic acid precipitates and is collected by filtration. 1H-NMR (DMSO-d6): δ=4.75 (bs, 2H); 5.99-6.05 (m, 1H); 6.98 (d, J=7.78 Hz, 1H); 7.19 (t, J=7.78 Hz, 1H); 7.25 (d, J=10.3 Hz, 1H); 7.40 (d, J=7.78 Hz, 1H); 13.0 (bs, 1H).

Workup

  1. concentrationpartially concentrated in vacuo
  2. customto remove MeOH
  3. additionmade acidic by addition of aq. HCl (1.0M)
  4. customThe desired carboxylic acid precipitates
  5. filtrationis collected by filtration

Sources & evidence

ORD record
ord-51eb9de6abf2419891d6e598571b7524
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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