Water → HCID 20672171, compound

HRID 1386491Notes

Reaction equation

HRID 1386491 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[CH3:16][C:17]1([CH3:29])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH3:28])([CH3:27])[CH2:19][CH2:18]1.O>ClCCl>[CH3:16][C:17]1([CH3:29])[CH2:18][CH2:19][C:20]([CH3:28])([CH3:27])[C:21]2[CH:22]=[C:23]([C:13](=[O:14])[CH2:12][C:9]3[CH:10]=[CH:11][C:6]([Br:5])=[CH:7][CH:8]=3)[CH:24]=[CH:25][C:26]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 811861,1,4,4-TetramethyltetralinHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 20672171HCID 20672171, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium trichloride (4.33 g, 32.5 mmol) and 4-bromophenylacetyl chloride (5.55 g, 23.2 mmol) are added successively at −30° C. to a solution of 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (4.36 g, 23.2 mmol) in 300 ml of dichloromethane. The temperature is allowed to rise to 0° C. in 30 minutes, the reaction mixture is poured over 400 ml of a volume to volume mixture of ice and water and this is extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and evaporated. The raw product is purified by crystallisation in hexane to obtain 5.69 g of a white solid, 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-oxo-2-ethyl]bromobenzene (yield=63%).

Workup

  1. extractionthis is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe raw product is purified by crystallisation in hexane

Sources & evidence

ORD record
ord-7345b03e1c314dd4b3711b15d52b347e
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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