Sodium Hydroxide → 1,4-Diethoxynaphthalene-2,3-dicarboxylic acid

HRID 889499Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17]([O:19]CC)=[O:18])[C:5]=1[C:22]([O:24]CC)=[O:23])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:15]([O:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:22]([OH:24])=[O:23])[C:6]=1[C:17]([OH:19])=[O:18])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of diethyl 1,4-bis(ethyloxy)-2,3-naphthalenedicarboxylate (1343 g, 3.73 mol) in ethanol (5.5 L) was added 2M sodium hydroxide solution (5.5 L, 11.0 mol). The reaction mixture was heated to reflux for 8 hours, with the reaction progress monitored by 1H-nmr spectroscopy. The mixture was then cooled to 0° C. for 18 hours before isolation of the crystallised solid by filtration, washing with ethanol (5 L) and drying in a vacuum oven at 60° C. to constant mass gave the desired product as a white solid (903.7 g, ˜11% water remains by Karl-Fischer, 62% yield).

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for 8 hours, with the reaction progress
washwashing with ethanol (5 L)
customdrying in a vacuum oven at 60° C. to constant mass

Sources & evidence

ORD record: ord-eea856753596458681e70fac1fb71827
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252833B2

Reaction notes

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