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Durene → 2-Acetyl-6-methoxynaphthalene

HRID 1030848
Notes
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Reaction equation

HRID 1030848 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[C:14]=2Br)[CH:9]=1)(=[O:7])[CH3:6].C1(C(=CC(=C(C=1)C)C)C)C>C(Cl)Cl>[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[CH:14]=2)[CH:9]=1)(=[O:7])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7269DureneHCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-one2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 775062-Acetyl-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

30 Grams of anhydrous aluminum chloride are added portionwise to a mixture made of 41.85 g of 2-acetyl-5-bromo-6-methoxynaphthalene, 22.15 g of durene and 180 ml of anhydrous methylene chloride cooled to -5° C., in such a manner that the temperature of 20° C. is not exceeded. The reaction mixture is kept for 2 hours at room temperature after the end of the addition and then it is worked as in example 1 obtaining 27.1 g of product with a yield equal to 90.6% calculated on the basis of the starting material 2-acetyl-5-bromo-6-methoxynaphthalene.

Workup

  1. customthat the temperature of 20° C.
  2. additionafter the end of the addition

Sources & evidence

ORD record
ord-b4a10eb295bd4f019ba365ffbfd34a06
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05107013

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes