Water → 4,4-Dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

HRID 2193821Notes

Reaction equation

HRID 2193821 reaction equation
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:7]1[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1.C(Cl)Cl.O>CCCCCCCC>[CH2:12]([C:11]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:33]2[CH:32]=[CH:31][S:30][C:29]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 585680009-([2,2'-Bithiophen]-3-yl)heptadecan-9-ol

Product 1

HCID 595825444,4-Dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent

Procedure

H2SO4 (9.38 mL) was added dropwise to 9-([2,2′-bithiophen]-3-yl)heptadecan-9-ol (IIe) (6.20 g, 15 mmol) in 200 ml n-octane under stirring at room temperature. After stirring for 12 h, CH2Cl2 (130 mL) and water (130 mL) were added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were successively washed with saturated NaHCO3 and brine. After drying over MgSO4, the solvent was removed in vacuo. The crude oil was purified with column chromatography (eluent hexane) to afford a pure dark yellow oil (Ie) (3.19 g, 52.9%). 1H-NMR (CDCl3): δ=7.14 (d, J=4.8 Hz, 2H), 6.93 (d, J=5.1 Hz, 2H), 1.87-1.79 (m, 4H), 1.40-1.06 (m, 24H), 0.95-0.82 (m, 6H).

Workup

  1. stirringAfter stirring for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic extracts were successively washed with saturated NaHCO3 and brine
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was purified with column chromatography (eluent hexane)
  8. customto afford a pure dark yellow oil (Ie) (3.19 g, 52.9%)

Sources & evidence

ORD record
ord-18d009546e0b4b0fa18a90103f7b2441
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

Loading…