1,4-Dihydroxy-2-naphthoic acid → 1-Hydroxy-4-(beta-ethylsulfonylethoxy)-2-naphthoic acid

HRID 126962Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.[CH2:34]([S:36]([CH2:39][CH2:40]O)(=[O:38])=[O:37])[CH3:35]>C(#N)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:35][CH2:34][S:36]([CH2:39][CH3:40])(=[O:38])=[O:37])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

Conditions

Temperature: 95 °C

Procedure

20.4 g (0.1 mol) of 1,4-dihydroxy-2-naphthoic acid and 19 g (0.1 mol) of p-toluenesulfonic acid were added to 200 ml of dehydrated toluene. To the mixture, 27.6 g (0.2 mol) of β-ethylsulfonylethanol was added dropwise for 30 minutes under heating at 95° C. with stirring. After heating with stirring for 7 hours, the mixture was cooled to 20° to 30° C. 100 ml of acetonitrile was added to the mixture, the solid deposited was separated by filtration to obtain 17.2 g (53%) of 1-hydroxy-4-(β-ethylsulfonylethoxy)-2-naphthoic acid.

Workup

temperatureAfter heating
stirringwith stirring for 7 hours
temperaturethe mixture was cooled to 20° to 30° C
customthe solid deposited was separated by filtration

Sources & evidence

ORD record: ord-85e1e635594244828529783664987b1d
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254212

Reaction notes

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