Water → HCID 49840164, compound

HRID 2193823Notes

Reaction equation

HRID 2193823 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][CH:13]([CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:7]1[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1.C(Cl)Cl.O>CCCCCCCC>[CH2:18]([CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[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)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 49840163HCID 49840163, compound

Product 1

HCID 49840164HCID 49840164, compound

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent

Procedure

H2SO4 (0.37 mL) was added dropwise to 7-([2,2′-bithiophen]-3-yl)-5-ethylpentadecan-7-ol (IId) (1.59 g, 3.79 mmol) in 50 ml n-octane under stirring at room temperature. After stirring for 12 h, CH2Cl2 (15 mL) and water (15 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 (Id) (0.852 g, 57%). 1H-NMR (CDCl3): δ=7.12 (d, J=4.8 Hz, 2H), 6.93 (d, J=4.8 Hz, 2H), 1.90 (t, 2H), 1.82 (m, 2H), 1.28-1.12 (m, 5H), 1.00-0.74 (m, 16H), 0.62 (t, 9H).

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 (Id) (0.852 g, 57%)

Sources & evidence

ORD record
ord-0d3c1f38798c4e07af5b235e8d3afb88
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

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