Ethyl vinyl ether → 6-(1-Ethoxy ethoxy)-2-naphthaldehyde

HRID 734165

Reaction equation

HRID 734165 reaction equation
OC1C=C2C(=CC=1)C=C(C=C)C=C2.[OH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18]2.[CH:27]([O:29][CH2:30][CH3:31])=[CH2:28]>>[CH2:27]([O:29][CH:30]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18]2)[CH3:31])[CH3:28]

Participants

4

Reactant 3

HCID 8023Ethyl vinyl etherHCID 27641106-Hydroxy-2-naphthaldehyde2×HCID 231357586-Ethenylnaphthalen-2-ol

Product 1

HCID 231357596-(1-Ethoxy ethoxy)-2-naphthaldehyde

Procedure

The synthesis of 6-hydroxy-2-vinylnaphthalene (HVN) was carried out by three step reactions starting from 6-hydroxy-2-naphthaldehyde. In the first step, 6-hydroxy-2-naphthaldeyde (HNAL) was protected with ethyl vinyl ether to give 6-(1-ethoxy ethoxy)-2-naphthaldehyde (EENAL). This was followed by the Wittig reaction of EENAL to yield 6-(1-ethoxy ethoxy)-2-vinylnaphthalene. Finally, this was deprotected using pyridinium p-toluenesulfonate to yield 6-hydroxy-2-vinylnaphthalene (HVN).

Sources & evidence

ORD record
ord-44e49d36b8344373abadf1d19721e492
Source dataset
uspto-grants-2009_09
Patent number
US07592125B2

Linked notes

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