Sodium Hydroxide → HCID 59609194, compound

HRID 2195100Notes

Reaction equation

HRID 2195100 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:14])[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](=[O:13])[C:2]1=2.[OH-].[Na+].[CH2:17]([CH:23]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C.O.[Zn]>[CH2:17]([CH:23]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][O:14][C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([O:13][CH2:24][CH:23]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 4277813HCID 4277813, compound

Product 1

HCID 59609194HCID 59609194, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.0 g, 4.54 mmol) and Zn powder (0.659 g, 10.1 mmol) were suspended in ethanol (10 mL). A solution of NaOH (3 g) in water (15 mL) was added. The resulting mixture was heated to reflux for 1 hour, after which 2-hexyldecyl(4-methylbenzenesulfonate) (3.86 g, 9.73 mmol) was added. The reaction was heated to reflux overnight. The reaction was cooled to room temperature and water (50 mL) was added. The reaction was extracted with ether, followed by separation and drying of the organic layer over MgSO4. Solvent was removed and the residue was purified by chromatography (10% dichloromethane in hexanes as eluent). The yield of the 4,8-bis[(2-hexyldecyl)oxy]-benzo[1,2-b:4,5-b′]dithiophene was 0.80 g (26%). 1H NMR (CDCl3, 500 MHz) δ=7.47 (d, J=2.75, 2H), 7.36 (d, J=2.75, 2H), 4.16 (m, 4H), 1.86 (m, 2H), 1.38-1.65 (m, 48H), 0.86 (m, 12H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction was heated
  4. temperatureto reflux overnight
  5. extractionThe reaction was extracted with ether
  6. customfollowed by separation
  7. dry with materialdrying of the organic layer over MgSO4
  8. customSolvent was removed
  9. customthe residue was purified by chromatography (10% dichloromethane in hexanes as eluent)

Sources & evidence

ORD record
ord-a87e544db3c7475ab46ddebb6c97023a
Source dataset
uspto-grants-2012_12
Patent number
US08334456B2

Reaction notes

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