Dimethyl 3,3'-(naphthalene-2,7-diyl)dibenzoate → 3,3'-(Naphthalene-2,7-diyl)dibenzoic acid

HRID 1484216Notes

Reaction equation

HRID 1484216 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=3)[C:14]([O:16]C)=[O:15])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26]C)=[O:25]>C1COCC1.CO.[OH-].[Na+]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=3)[C:14]([OH:16])=[O:15])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([OH:26])=[O:25]

Participants

5

Reactant 1

HCID 71283629Dimethyl 3,3'-(naphthalene-2,7-diyl)dibenzoate

Product 1

HCID 706984423,3'-(Naphthalene-2,7-diyl)dibenzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.0 g of dimethyl 3,3′-(naphthalene-2,7-diyl)dibenzoate was dissolved in 60 mL of mixed solvent of THF and MeOH (v/v=1:1), 20 mL of 2N NaOH aqueous solution was added. The mixture was stirred at room temperature overnight. After the organic phase was removed, the aqueous phase was acidified with dilute hydrochloric acid to give white precipitate, which was filtered and washed with water several times. Yield: 1.71 g, 92%. 1H NMR (300 MHz, DMSO-d6): δ 7.65 (t, 2H), 7.92 (d, 2H), 7.98 (d, 2H), 8.09 (m, 4H), 8.38 (m, 2H), 8.43 (d, 2H).

Workup

  1. additionwas added
  2. customAfter the organic phase was removed
  3. customto give white precipitate, which
  4. filtrationwas filtered
  5. washwashed with water several times

Sources & evidence

ORD record
ord-b6504b9e8b9d4fa1967f5d7d58d1b576
Source dataset
uspto-grants-2016_08
Patent number
US09421514B2

Reaction notes

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