Hexane → HCID 71245442, compound

HRID 575501Notes

Reaction equation

HRID 575501 reaction equation
[CH3:1][O:2][C:3]1[C:18]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH:12]=[C:11]([O:19][CH3:20])[C:10]=2[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.[C:21](Cl)(=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[Cl-].[Cl-].[Cl-].[Al+3].CCCCCC>ClCCl>[CH3:20][O:19][C:11]1[C:10]2[C:6]3[S:7][C:8]([C:21](=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:9][C:5]=3[CH:4]=[C:3]([O:2][CH3:1])[C:18]=2[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8166Dodecanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 712456764,9-Dimethoxynaphtho[1,2-b:5,6-b']dithiophene

Product 1

HCID 71245442HCID 71245442, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,9-Dimethoxynaphtho[1,2-b:5,6-b′]dithiophene (0.90 g, 3.0 mmol) was solubilized in anhydrous dichloromethane (20 mL). Dodecanoyl chloride (0.765 g, 3.5 mmol) was then added and stirring was continued for 10 minutes at this temperature. Aluminum trichloride (0.465 g, 3.5 mmol) was then added in 3 portions. The mixture was stirred overnight at room temperature. The mixture was cooled in ice water and extracted with chloroform (200 mL) and washed with water (100 mL) and brine (50 mL). After the solvent was removed, the residual was purified using a silica column with dichloromethane:hexane (1/3) to give compound 1-(4,9-dimethoxynaphtho[1,2-b:5,6-b′]dithiophen-2-yl)dodecan-1-one as a pale yellow solid (0.78 g, ˜54% yield). 1H NMR (500 MHz, CDCl3): δ 8.72 (s, 1H), 7.69 (d, J=5.5 Hz, 1H), 7.50 (m, 2H), 7.42 (s, 1H), 4.24 (s, 3H), 4.22 (s, 3H) 3.07. (t, J=7.0 Hz, 2H), 1.83 (m, 2H), 1.39 (m, 18H); 0.88 (m, J=6.0 Hz, 3H).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with chloroform (200 mL)
  3. washwashed with water (100 mL) and brine (50 mL)
  4. customAfter the solvent was removed
  5. customthe residual was purified

Sources & evidence

ORD record
ord-b3c7173ef1534b90887d0c10e82ba97d
Source dataset
uspto-grants-2015_05
Patent number
US09035004B2

Reaction notes

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