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Benzene → 2-(4-Methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone

HRID 1447673
Notes
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Reaction equation

HRID 1447673 reaction equation
C[C:2](C)([O-:4])C.[K+].[CH3:7][CH:8]1[CH2:16][C:15]2[C:10](=[C:11]([Cl:26])[C:12]([Cl:25])=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:14]=2)[C:9]1=[O:27].[CH:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(O)(C)(C)C>[CH3:2][O:4][C:28]1[CH:33]=[CH:32][C:31]([C:8]2([CH3:7])[CH2:16][C:15]3[C:10](=[C:11]([Cl:26])[C:12]([Cl:25])=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:14]=3)[C:9]2=[O:27])=[CH:30][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 124236142-Methyl-5-benzyloxy-6,7-dichloro-1-indanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 124236152-(4-Methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 6386
tert-Butanol
Solvent
2×

Conditions

Temperature
25 °C

Procedure

Potassium tert-butoxide (8.42 g., 0.075 mole) dissolved in tert-butanol (450 ml.) is added to a refluxing solution of 2-methyl-5-benzyloxy-6,7-dichloro-1-indanone (16.1 g., 0.05 mole) in tert-butanol (150 ml.)-benzene (600 ml.), refluxing is continued for 2.5 hrs., then 4,4'-dimethoxydiphenyliodonium chloride (37.66 g., 0.10 mole) is added and refluxing is continued for 3 hrs. The reaction mixture is cooled to 25° C., 500 ml. water added, and the mixture concentrated in vacuo to give a brown oil which on ether extraction, drying over anhydrous magnesium sulfate, removal of the ether and chromatographing of the residue on silica gel with chloroform gives 3.44 g. of 2-(4-methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone which melts at 115°-119° C. and is used without further purification.

Workup

  1. temperaturerefluxing
  2. temperaturerefluxing
  3. waitis continued for 3 hrs
  4. concentrationthe mixture concentrated in vacuo
  5. customto give a brown oil which
  6. extractionon ether extraction
  7. dry with materialdrying over anhydrous magnesium sulfate, removal of the ether and chromatographing of the residue on silica gel with chloroform
  8. customgives 3.44 g
  9. customof 2-(4-methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone which melts at 115°-119° C. and is used without further purification

Sources & evidence

ORD record
ord-5921716aea884320a57bc9c02d04f217
Source dataset
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04177285

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes