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

HRID 49642
Notes
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Reaction equation

HRID 49642 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 517044Potassium AcetateHCID 129913627-(2-naphthoyl)-3-methyl-5,6-dihydro-2(4H)-benzofuranone

Product 1

HCID 9901064alpha-Methyl-3(2-naphthoyl)benzene Acetic Acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

  1. additionwas added to a reactor
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. customToluene layer separated
  4. dry with materialwas dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customThe crude product was purified by column chromatograph on silica gel
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes