Acetone → 2-Acetylnaphthalene

HRID 436671Notes

Reaction equation

HRID 436671 reaction equation
C([O:4][CH:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH3:6])(=O)C.S(=O)(=O)(O)O.CC(C)=O>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)(=[O:4])[CH3:6]

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 98777802-(1-Acetoxyethyl)naphthalene

Product 1

HCID 71222-Acetylnaphthalene

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 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. customupon base hydrolysis

Sources & evidence

ORD record
ord-57176524ce064f1fa3b7420a16baec01
Source dataset
uspto-grants-1977_02
Patent number
US04009197

Reaction notes

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