Sodium Acetate → 2-Acetylnaphthalene

HRID 436670Notes

Reaction equation

HRID 436670 reaction equation
Br[CH:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)[CH3:3].[C:14]([O-:17])(=[O:16])[CH3:15].[Na+]>C(O)(=O)C>[C:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=[O:16])[CH3:3].[C:14]([O:17][CH:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)[CH3:3])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 186782542-(1-Bromoethyl)naphthalene

Product 2

HCID 71222-AcetylnaphthaleneHCID 98777802-(1-Acetoxyethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Acetylnaphthalene is prepared by treating 2-(1-bromoethyl)naphthalene, prepared as described above, with sodium acetate in acetic acid to afford 2-(1-acetoxyethyl)naphthalene which upon base hydrolysis furnishes the 2-(1-hydroxyethyl)naphthalene. The latter is oxidized with an equivalent of chromium trioxide in glacial acetic acid, or 8N sulfuric acid and acetone to furnish 2-acetylnaphthalene. 2-Carboxynaphthalene is prepared from 2-acetylnaphthalene by treating the latter with aqueous sodium hypochlorite. The 2-carboxynaphthalene is treated with diborane in an ether, such as diglyme (diethyleneglycol dimethyl ether), to yield 2-hydroxymethylnaphthalene.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-d57802848ad54e4da6884e8e7a7ff1a0
Source dataset
uspto-grants-1977_02
Patent number
US04009197

Reaction notes

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