1-Octanol → HCID 12118488, compound

HRID 540963Notes

Reaction equation

HRID 540963 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1.[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 1402493-MethoxythiopheneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12118488HCID 12118488, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-methoxythiophene (7.28 g, 63.76 mmol), 1-octanol (20.09 mL, 127.53 mmol), p-toluenesulfonic acid monohydrate (1.21 g, 6.38 mmol) and 60 mL toluene was heated in a 130° C. bath for 15 hours under argon. After dichloromethane/water extraction, the organic layer was dried over anhydrous Na2SO4. After solvent evaporation, the residue was purified by column chromatography (silica gel 3:1 hexane:dichloromethane) to give 2′ as a colorless solid (13.00 g, 96%). 1H NMR (CDCl3, 300 MHz, ppm): δ 7.18-7.21 (m, 1H), 6.78-6.80 (m, 1H), 6.25-6.26 (m, 1H), 3.97 (t, 2H, 6.6 Hz), 1.76-1.85 (m, 2H), 1.33-1.48 (m, 10H), 0.91-0.95 (m, 3H).

Workup

  1. extractionAfter dichloromethane/water extraction
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. customAfter solvent evaporation
  4. customthe residue was purified by column chromatography (silica gel 3:1 hexane:dichloromethane)

Sources & evidence

ORD record
ord-897ce6cc503641168b810239306882bb
Source dataset
uspto-grants-2014_10
Patent number
US08871884B2

Reaction notes

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