Sodium Hydroxide → HCID 66906295, compound

HRID 709584Notes

Reaction equation

HRID 709584 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[C:5](=[C:10]([O:14][CH:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH3:16])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[CH:15]([O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:27])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66906390HCID 66906390, compound

Product 1

HCID 66906295HCID 66906295, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(1-naphthalen-2-yl-ethoxy)-phthalic acid dimethyl ester (0.9 g, 2.5 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 2 h. The mixture was cooled and the solvent was removed under vacuum. The residue was dissolved in water (100 mL) and washed with CH2Cl2 (3×100 mL), acidified (HCl), and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 0.50 g of 3-(1-naphthalen-2-yl-ethoxy)-phthalic acid, in 60% yield; 1H NMR (DMSO-d6) δ 1.60 (d, J=6.2 Hz, 3H), 5.79 (q, J=6.2 Hz, 1H), 7.21-7.31 (m, 2H), 7.38 (dd, J=7.1 Hz, J=1.3 Hz, 1H), 7.46-7.57 (m, 3H), 7.83-7.93 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in water (100 mL)
  6. washwashed with CH2Cl2 (3×100 mL)
  7. extractionextracted with ethyl acetate (3×75 mL)
  8. washThe combined organic extracts were washed with water (3×75 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-44fd7bc1e3ac442cac17cdb9be3d5ee7
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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