Tetraethyl 5,5'-(naphthalene-2,7-diyl)diisophthalate → 5,5'-(Naphthalene-2,7-diyl)diisophthalic acid

HRID 1484220Notes

Reaction equation

HRID 1484220 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([C:22]([O:24]CC)=[O:23])[CH:14]=[C:15]([CH:21]=3)[C:16]([O:18]CC)=[O:17])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:27]1[CH:28]=[C:29]([C:38]([O:40]CC)=[O:39])[CH:30]=[C:31]([CH:37]=1)[C:32]([O:34]CC)=[O:33]>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]([C:22]([OH:24])=[O:23])[CH:14]=[C:15]([CH:21]=3)[C:16]([OH:18])=[O:17])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:27]1[CH:37]=[C:31]([C:32]([OH:34])=[O:33])[CH:30]=[C:29]([CH:28]=1)[C:38]([OH:40])=[O:39]

Participants

5

Reactant 1

HCID 71283170Tetraethyl 5,5'-(naphthalene-2,7-diyl)diisophthalate

Product 1

HCID 706984365,5'-(Naphthalene-2,7-diyl)diisophthalic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.0 g of tetraethyl 5,5′-(naphthalene-2,7-diyl)diisophthalate 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 a white precipitate, which was filtered and washed with water several times. Yield: 1.46 g, 91%. 1H NMR (300 MHz, DMSO-d6): δ 7.95 (d, 2H), 8.11 (d, 2H), 8.53 (m, 8H).

Workup

  1. additionwas added
  2. customAfter the organic phase was removed
  3. filtrationwas filtered
  4. washwashed with water several times

Sources & evidence

ORD record
ord-9e26960f89d042698604e5a44c5a72a7
Source dataset
uspto-grants-2016_08
Patent number
US09421514B2

Reaction notes

Loading…