Diethyl Ether → 1-Naphthol

HRID 420012

Reaction equation

HRID 420012 reaction equation
CNCC[C@H]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12)[C:6]1[S:10][CH:9]=[CH:8][CH:7]=1.CC[O:24]CC>>[S:10]1[CH:9]=[CH:8][CH:7]=[C:6]1[OH:24].[C:12]1([OH:11])[C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 60835Duloxetine

Product 2

HCID 70051-NaphtholHCID 10909502Thiophen-2-ol

Procedure

Duloxetine is acid labile, and acid hydrolysis of its ether linkage results in a thienyl alcohol and 1-naphthol. 50% of a dosage is hydrolyzed to 1-naphthol within one hour at a pH of 1.0, which is achieved under fasting conditions. At a pH of 2.0, 10% of the dosage degrades to 1-Naphthol in one hour and at a pH of 4.0, 10% degradation would take up to 63 hours. The reaction scheme showing the conversion of duloxetine to 1-naphthol and its thienyl derivative is shown below.

Sources & evidence

ORD record
ord-de1aac75d8c34331899b85869fa93e77
Source dataset
uspto-grants-2012_01
Patent number
US08093408B2

Linked notes

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