Toluene → HCID 66609802, compound

HRID 1909841Notes

Reaction equation

HRID 1909841 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C.C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:1]([O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 81841-UndecanolHCID 856102-MethoxythiopheneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 66609802HCID 66609802, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methoxythiophene (5.13 g, 44.93 mmol), n-C11H23OH (15.5 g, 89.87 mmol), toluene (50 mL), and p-toluenesulfonic acid monohydrate (0.85 g, 4.47 mmol) was heated to reflux under nitrogen for 19 hours. After cooling to room temperature, the reaction mixture was poured into water (150 mL), and the mixture was extracted with dichloromethane (DCM, 250 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to flash column on silica gel with hexane as eluent (slowly up to a hexane:DCM (8:2, v/v) mixture), leading to a colorless oil as the product (7.76 g, 67.9%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 19 hours
  3. extractionthe mixture was extracted with dichloromethane (DCM, 250 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-131cf62fb2804461aecc9fde7ed67d68
Source dataset
uspto-grants-2013_12
Patent number
US08598575B2

Reaction notes

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