Hexane → 6-Decyl-3-methylthio-2-methoxynaphthalene

HRID 1476369Notes

Reaction equation

HRID 1476369 reaction equation
CCCCCC.[CH2:7]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([O:27][CH3:28])[CH:21]=[CH:20]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:29][S:30]SC.[Cl-].[NH4+]>C1COCC1>[CH2:7]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([O:27][CH3:28])[C:21]([S:30][CH3:29])=[CH:20]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8058HexaneHCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 867043812-Decyl-6-methoxynaphthalene

Product 1

HCID 867043856-Decyl-3-methylthio-2-methoxynaphthaleneYield 110.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A hexane solution of 1.57 Mn—BuLi (28 ml, 44 mmol) was added to a THF (100 ml) solution of 6-n-decyl-2-methoxynaphthalene (compound (3)-64) (12 g, 40 mmol) at −78° C., and the solution was stirred at room temperature for 1 hour. Dimethyl disulfide (4.4 ml, 48 mmol) was added to the solution at −78° C., and the solution was stirred at room temperature for 18 hours. The reaction solution was added to a saturated ammonium chloride aqueous solution (50 ml), and extracted with ether (30 ml×3). The extracted solutions obtained by repeating the extraction 3 times were collected, washed with a saturated saline water (30 ml×3), and dried with MgSO4. The dried product was condensed with an evaporator to obtain 6-n-decyl-3-methylthio-2-methoxynaphthalene (compound (4)-64) (15.2 g, quantitative) as a yellow oil. The compound can be used in the subsequent reaction without performing further refining.

Workup

  1. stirringthe solution was stirred at room temperature for 18 hours
  2. extractionextracted with ether (30 ml×3)
  3. customThe extracted solutions obtained
  4. extractionthe extraction 3 times
  5. customwere collected
  6. washwashed with a saturated saline water (30 ml×3)
  7. dry with materialdried with MgSO4
  8. customcondensed
  9. customwith an evaporator

Sources & evidence

ORD record
ord-0bfef4172cb246de9874c91885756eb5
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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