1-Dodecanol → HCID 59523070, compound

HRID 1424772Notes

Reaction equation

HRID 1424772 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][S: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][CH2:18]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[N:4]=[CH:5][S:6][CH:7]=1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 18622380HCID 18622380, compound

Product 1

HCID 59523070HCID 59523070, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4.0 g (34.7 mmol) of 4-methoxythiazole (9), 12.8 g (68.7 mmol) of dodecanol, 0.7 g (3.7 mmol) of p-toluenesulfonic acid monohydrate, and 75 mL of toluene was heated at 130° C. for 24 hours. The mixture was cooled to room temperature and purified by flash chromatography (silica gel, 5.5×30 cm, methylene chloride). The resulting oily solid was recrystallized from 20 mL of cold pentane to give 5.15 g (55% yield) of 4-dodecyloxythiazole (10) as a colorless solid. 1H NMR (500 MHz) δ 8.58 (d, 1H, J=2.3 Hz), 6.13 (d, 1H, J=2.3 Hz), 4.13 (t, 2H, J=6.6 Hz), 1.83 (m, 2H), 1.49-1.28 (m, 18H), 0.90 (t, 3H, J=7.0).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurified by flash chromatography (silica gel, 5.5×30 cm, methylene chloride)
  3. customThe resulting oily solid was recrystallized from 20 mL of cold pentane

Sources & evidence

ORD record
ord-f93de5df932745469caf5050dd6a7a9b
Source dataset
uspto-grants-2015_01
Patent number
US08927971B2

Reaction notes

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