1,1,4,4-Tetramethyltetralin → Methyl 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoate

HRID 583058Notes

Reaction equation

HRID 583058 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3]1.[Cl-].[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][C:5]([CH3:13])([CH3:12])[C:6]2[CH:7]=[C:8]([C:23]([C:22]3[CH:26]=[CH:27][C:19]([C:18]([O:17][CH3:16])=[O:28])=[CH:20][CH:21]=3)=[O:24])[CH:9]=[CH:10][C:11]1=2

Participants

5

Reactant 3

HCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) ChlorideHCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 10784070Methyl 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoateYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene (10.0 g, 53.2 mmol) and terephthalic acid monomethyl ester chloride (10.0 g, 50.5 mmol) were dissolved in dichloromethane (50 ml) and the mixture was added with AlCl3 (14.3 g, 107.5 mmol) over 10 minutes under ice cooling. After reflux for 1 hour, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water and saturated brine and dried, and then concentrated to give methyl 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoate (Compound 43, 18.5 g, 99%). A part of the product was recrystallized from ethyl acetate.

Workup

  1. temperatureAfter reflux for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and saturated brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3002828f44b4c71823598e49dca6f14
Source dataset
uspto-grants-1999_07
Patent number
US05929069

Reaction notes

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