Tetralin → HCID 18551890, compound

HRID 1266677Notes

Reaction equation

HRID 1266677 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17]>ClCCl>[CH3:17][CH:16]([CH3:18])[C:15]([C:11]1[CH:12]=[CH:13][C:14]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1)=[O:19]

Participants

5

Conditions

Temperature
0 °C

Procedure

Aluminium chloride (28.0 g, 0.21 mole) was suspended in 200 ml of anhydrous dichloromethane (200 ml) and cooled to 0° C. A solution of 1,2,3,4-tetrahydronaphthalene (26.5 g, 0.2 mole) and isobutyryl chloride (21.3 g, 0.20 mole) in 50 ml of anhydrous dichloromethane was slowly added to this suspension. After the addition was completed, the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was poured onto 300 g of ice water, and the organic layer was separated. The organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml). After drying over anhydrous magnesium sulfate the solution was concentrated under reduced pressure. The yield of 2-methyl-1-(5,6,7,8-tetrahydro-2-naphthalenyl)-1-propanone was 39.7 g or 98%.

Workup

  1. additionAfter the addition
  2. customthe organic layer was separated
  3. washThe organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml)
  4. dry with materialAfter drying over anhydrous magnesium sulfate the solution
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c5a7ef16c024f88bce30f8b2078fcb8
Source dataset
uspto-grants-2003_04
Patent number
US06548710B2

Reaction notes

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