Sodium Hydroxide → HCID 18930353, compound

HRID 552573Notes

Reaction equation

HRID 552573 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:17])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 43532221HCID 43532221, compound

Product 1

HCID 18930353HCID 18930353, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(5-Chloropentyloxy)benzoic acid methyl ester (1.14 g. 4.44 mmol) is dissolved in MeOH (15 mL) and 5 N NaOH (10 mL) is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the residue is dissolved in water, acidified with concentrated hydrochloric acid to pH=1.0. This solution is extracted with CH2Cl2, dried over Na2SO4, filtered and evaporated. The resulting material is recrystallized from hexane/CH2Cl2, filtered and dried, to provide 829 mg (77%). NMR (CDCl3): δ 8.05 (d, 2H, J=9 Hz), 6.93 (d, 2H, J=9 Hz), 4.05 (t, 2H, J=6 Hz), 3.57 (t, 2H, J=6 Hz), 4.85 (m, 4H), 1.65 (m, 2H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in water
  3. extractionThis solution is extracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting material is recrystallized from hexane/CH2Cl2
  8. filtrationfiltered
  9. customdried
  10. customto provide 829 mg (77%)

Sources & evidence

ORD record
ord-ff0b8f8860e444afac6c8e9cd530874b
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Reaction notes

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