Hydrochloric Acid → 2-Methoxy-6-dodecanoylnaphthalene

HRID 1788339Notes

Reaction equation

HRID 1788339 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:17](Cl)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl.[N+](C1C=CC=CC=1)([O-])=[O:32]>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:17](=[O:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=2)[CH:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 71192-MethoxynaphthaleneHCID 7416NitrobenzeneHCID 81921-ChlorododecaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 689053702-Methoxy-6-dodecanoylnaphthaleneYield 64.2%

Conditions

Temperature
5 °C

Procedure

2-Methoxynaphthalene (30.1 g, 0.19 mol) was added to a solution of aluminum chloride (32.9 g, 0.25 mol) in anhydrous nitrobenzene under a nitrogen atmosphere. To the mixture was slowly added dropwise lauryl chloride (41.6 g, 0.19 mol) at 10-13° C. over 15 minutes. The resulting mixture was stirred at 5° C. for 2 hours and at room temperature for 12 hours. The reaction mixture was poured into 300 ml of 3M HCl at 0° C., extracted with chloroform, and sufficiently washed with brine. The solvents were removed by evaporation under reduced pressure. The residue was dissolved in chloroform and washed with 0.1M NaOH. The mixture was evaporated to remove the chloroform, followed by recrystallization from ethanol to give the title compound (41.5 g, yield: 64.2%).

Workup

  1. extractionextracted with chloroform
  2. washsufficiently washed with brine
  3. customThe solvents were removed by evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with 0.1M NaOH
  6. customThe mixture was evaporated
  7. customto remove the chloroform
  8. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-29af8fcf6b5d4a7ebf5b3ffd1d149c60
Source dataset
uspto-grants-2009_03
Patent number
US07511167B2

Reaction notes

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