Citric Acid → 1,5-Bis-benzyloxy-naphthalene-2-carboxylic acid

HRID 70008Notes

Reaction equation

HRID 70008 reaction equation
C([O:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:10])C1C=CC=CC=1.CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH2:30]([O:29][C:12]1[C:13]2[C:18](=[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:9]([OH:10])=[O:8])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67119827HCID 67119827, compound

Product 1

HCID 681632351,5-Bis-benzyloxy-naphthalene-2-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,5-Bis-benzyloxy-naphthalene-2-carboxylic acid benzyl ester (0.556 g, 1.17 mmol), MeOH (6.4 mL) and NaOH (1.25 mL), H2O (65.0 mL) and citric acid (0.28 g, 1.5 mmol) Yield: 0.507 g creamy white solid (92% yield). 1H NMR (400 MHz CDCl3) δ 5.23 (s, 2H), δ 5.28 (s, 2H), δ 7.06 (d, J=7.3 Hz, 1H), δ 7.38-7.55 (m, 11H), δ 7.83 (d, J=8.7 Hz, 1H), δ 8.08 (d, J=8.7 Hz, 1H), δ 8.26 (d, J=8.7 Hz, 1H).

Sources & evidence

ORD record
ord-9cfd1ae9cf9a488d8f7777b1c917c3ac
Source dataset
uspto-grants-2014_09
Patent number
US08822515B2

Reaction notes

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