Hydrochloric Acid → alpha-Methyl-3(2-naphthoyl)benzene Acetic Acid

HRID 49642Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[CH2:14][CH2:15][CH2:16][C:17]2[C:21]=1[O:20][C:19](=[O:22])[C:18]=2[CH3:23])=[O:12].[K+].C([O-])(=O)C.C1(C)C=CC=CC=1.Cl>O>[CH3:23][CH:18]([C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:12])[CH:21]=1)[C:19]([OH:22])=[O:20]

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 7-(2-naphthoyl)-3-methyl-5,6-dihydro-2(4H)-benzofuranone (10 g) and acetic acid potassium salt (0.3 g) was added to a reactor and stirred for 1 hr at 220° C. The reaction mixture was cooled down to room temperature. Toluene and water were added to the reaction mixture and acidified to pH 2 with 5% hydrochloric acid. Toluene layer separated was dried over anhydrous MgSO4, filtered and evaporated to give crude product. The crude product was purified by column chromatograph on silica gel by eluting with a mixture of ethylacetate and n-hexane (1:5) to give the desired product (9:42 g, 94 % .

Workup

additionwas added to a reactor
temperatureThe reaction mixture was cooled down to room temperature
customToluene layer separated
dry with materialwas dried over anhydrous MgSO4
filtrationfiltered
customevaporated
customto give crude product
customThe crude product was purified by column chromatograph on silica gel
washby eluting with a mixture of ethylacetate and n-hexane (1:5)

Sources & evidence

ORD record: ord-1f4befc33ffa492db518647e07a976d7
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706917B1

Reaction notes

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