2-Acetylnaphthalene → 2-Naphthoic acid

HRID 2071846Notes

Reaction equation

HRID 2071846 reaction equation
[C:1]([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:3])C.Cl[O-].[Na+].[C:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)([OH:19])=[O:18].B#B>COCCOCCOC.CCOCC>[C:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)([OH:19])=[O:18].[OH:3][CH2:1][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 71222-AcetylnaphthaleneHCID 71232-Naphthoic acidHCID 6328200DiboronHCID 23665760Sodium Hypochlorite

Product 2

HCID 71232-Naphthoic acidHCID 741282-Naphthalenemethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent

Procedure

2-Acetylnaphthalene is prepared by treating 2-(1'-bromoethyl)naphthalene, prepared as described above, wtih sodium acetate in acetic acid to afford 2-(1'-acetonyethyl)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.

Sources & evidence

ORD record
ord-aff660d0383249f7ba837dce5845950d
Source dataset
uspto-grants-1977_09
Patent number
US04048330

Reaction notes

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