Sodium Hydroxide → HCID 66997832, compound

HRID 2064781Notes

Reaction equation

HRID 2064781 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 sodium hydroxide (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 hydrochloric acid (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 hydrochloric acid (1.0 M)
  3. filtrationThe obtained precipitate is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7be0600d7e7149cf8ede2bb82b3e42dc
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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