Hydrochloric Acid → HCID 68460107, compound

HRID 502615Notes

Reaction equation

HRID 502615 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH3:13])=[CH:5][CH:4]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:18](Cl)(=[O:20])[CH3:19].Cl>ClCCCl>[CH3:1][O:2][C:3]1[C:4]([C:18](=[O:20])[CH3:19])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH3:13])[C:11]=2[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 216367161,2,3,4-Tetrahydro-7-methoxy-1-methylnaphthalene

Product 1

HCID 68460107HCID 68460107, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirring solution of 7-methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene (6.3 g, 35.74 mmol) in 60 mL 1,2-dichloroethane at 0° C. under nitrogen as added aluminium trichloride (5.24 g, 39.32 mmol), followed by acetyl chloride (2.8 mL, 39.32 mmol). The resulting mixture was stirred for 18 hours at room temperature, then was poured into cold 5% aqueous HCl and extracted with methylene chloride. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield 5.1 g of 1-(3-methoxy-5-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone, MP=48-50° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c505fb52e764d4e9e30bc90a8c0d45e
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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