Sodium Hydroxide → HCID 66997832, compound

HRID 560323Notes

Reaction equation

HRID 560323 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:17])=[C:10]2[O:14][CH:13]([O:15][CH3:16])[CH2:12][C:11]=12)=[O:5])C.[OH-].[Na+]>CO.O>[Cl:17][C:9]1[CH:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:11]2[C:10]=1[O:14][CH:13]([O:15][CH3:16])[CH2:12]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66998604HCID 66998604, compound

Product 1

HCID 66997832HCID 66997832, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 7-chloro-2-methoxy-2,3-dihydro-benzofuran-4-carboxylic acid ethyl ester (1.17 mmol) and NaOH (1.75 mmol) in MeOH (1.3 mL) and water (1.3 mL) is heated to 55° C. for 90 min. The mixture is concentrated in vacuo and made acidic by addition of aq. HCl (1.0 M). The obtained precipitate is filtered off and dried in vacuo to give the desired product. 1H-NMR (DMSO-d6): δ=13.1 (bs, 1H); 7.45 (d, J=8.3 Hz, 1H); 7.38 (d, J=8.5 Hz, 1H); 5.87 (d, J=6.3 Hz, 1H); 3.67 (dd, J=18.1 Hz, J=6.0 Hz, 1H); 3.47 (s, 3H); 3.30 (d, 1H).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionmade acidic by addition of aq. HCl (1.0 M)
  3. filtrationThe obtained precipitate is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ce413441c9b640e39d274b46e6d053c6
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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