Toluene → HCID 14473214, compound

HRID 2106897Notes

Reaction equation

HRID 2106897 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][CH2:15]C.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.CO.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][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 1140TolueneHCID 89141-NonanolHCID 1402493-Methoxythiophene

Product 1

HCID 14473214HCID 14473214, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 21867641Toluene methanolSolvent

Procedure

25 cm3 of 3-methoxythiophene (0.25 mole), 50 cm3 of 1-nonanol (0.28 mol) and 30 cm3 of toluene were heated to 120° C. together with 1 g of p-toluenesulfonic acid, and about 9.5 cm3 of a methanol/toluene mixture were distilled off over a period of 3 hours. The workup was carried out as described in Example 1. Fractionation through a 30 cm Vigreux column at 0.26 mbar gave 42 g of 3-n-nonyloxythiophene of boiling point 102° to 105° C., which corresponds to 74% of the theoretical yield. 1H-NMR and mass spectrum confirm the structure.

Workup

  1. distillationwere distilled off over a period of 3 hours

Sources & evidence

ORD record
ord-77edb444929b49f49e8408e5a403ff56
Source dataset
uspto-grants-1990_06
Patent number
US04931568

Reaction notes

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