Water → 3-n-Propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 1744910Notes

Reaction equation

HRID 1744910 reaction equation
[CH3:1][CH2:2][CH2:3]I.C([O:7][C:8]1[C:9](/C(/CC)=C(/F)\C=C\C(\C)=C\C(OCC)=O)=[CH:10][C:11]2[C:12]([CH3:21])([CH3:20])[CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[C:16]=2[CH:17]=1)C.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH3:21])([CH3:20])[CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[C:16]=2[CH:17]=1)[CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 86593751Ethyl (2E,4E,6E)-7-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoate2×

Product 1

HCID 222261103-n-Propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Propyl iodide (4.9 mL, 50 mmol) was added to a stirring suspension of 6-hydroxy-1,2,3,4-tetrahydronaphthalene (Intermediate 1, 2.07 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), in acetone (50 mL), and the mixture was stirred at reflux for 14 h. The solution was poured into a separatory funnel, water was added, and the products were extracted three times with hexane. The combined organic layers were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound as a yellow oil.

Workup

  1. temperatureat reflux for 14 h
  2. additionThe solution was poured into a separatory funnel
  3. extractionthe products were extracted three times with hexane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-610e6411238a41a2ba062db119810002
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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