Propionyl chloride → 1-(3-Methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

HRID 1883273Notes

Reaction equation

HRID 1883273 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]2([CH3:25])[CH3:24]>C(Cl)Cl>[CH3:10][O:11][C:12]1[C:21]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:20][C:19]2[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103310036-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene2×

Product 1

HCID 235108141-(3-Methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following General Procedure A and using AlCl3 (3.7 g, 27.5 mmol), CH2Cl2 (40 mL), propionyl chloride (2.4 mL, 27.5 mmol), and 6-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (Intermediate 2, 5.0 g, 22.9 mmol) in CH2Cl2 (10 mL) at ambient temperature for 1.5 h followed by recrystallization from Et2O, the title compound was obtained as a white solid (5.4 g, 86%).

Workup

  1. customat ambient temperature
  2. customfor 1.5 h
  3. customfollowed by recrystallization from Et2O

Sources & evidence

ORD record
ord-867686cc20ac436abfda83b79a26cd7d
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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