Water → HCID 10616923, compound

HRID 583057Notes

Reaction equation

HRID 583057 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClCCl>[CH3:12][C:9]1([CH3:13])[CH2:10][CH2:11][C:2]([CH3:14])([CH3:1])[C:3]2[CH:4]=[C:5]([C:20]([C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[N+:15]([O-:17])=[O:16])=[O:21])[CH:6]=[CH:7][C:8]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 118752-Nitrobenzoyl chlorideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10616923HCID 10616923, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (10.0 g, 53.2 mmol) and o-nitrobenzoic acid chloride (9.4 g, 50.5 mmol) were dissolved in dichloromethane (50 ml), and the mixture was added with AlCl3 (14.3 g) portionwise and then heated under reflux for 1 hour and 30 minutes. The reaction mixture was poured into water and extracted with dichloromethane and dried, and then the solvent was evaporated to give a crude product (21.59 g). This product was purified by silica gel column chromatography (AcOEt:n-hexane=1:10) to give (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl-2-nitrobenzene (Compound 37, 7.5 g, 42%). This product was further recrystallized from n-hexane.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour and 30 minutes
  3. extractionextracted with dichloromethane
  4. customdried
  5. customthe solvent was evaporated
  6. customto give a crude product (21.59 g)
  7. customThis product was purified by silica gel column chromatography (AcOEt:n-hexane=1:10)

Sources & evidence

ORD record
ord-07ff2070a42b421e8fc0d7ab5ac197d4
Source dataset
uspto-grants-1999_07
Patent number
US05929069

Reaction notes

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