Water → 2-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinoline
Reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C1(C)C=CC(S(O[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:25]=2)(=O)=O)=CC=1.C(N(CC)CC)C.O>C(Cl)Cl>[OH:36][CH:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-hydroxymethylquinoline (8 g, 0.05 mol) and 3-(1-hydroxyhexyl)benzyl p-toluenesulfonate (18.2 g, 0.05 mol; prepared as in Example 17) in methylene chloride (200 ml) containing triethylamine (15 ml) was stirred at 0° C. for 4 hours, and then allowed to warm up to room temperature. This mixture was stirred for two more hours at this temperature, and then poured into water. The organic layer was separated and washed with dilute sodium hydroxide solution, water and brine. After drying the organics, all volatiles were removed to obtain the crude product as a yellowish brown liquid. This was purified by chromatography on silica gel using 15% ethyl acetate in hexanes to get the pure product as a clear, light yellow liquid (9 g, 52% yield).
Workup
- temperatureto warm up to room temperature
- stirringThis mixture was stirred for two more hours at this temperature
- customThe organic layer was separated
- washwashed with dilute sodium hydroxide solution, water and brine
- customAfter drying the organics, all volatiles
- customwere removed
- customto obtain the crude product as a yellowish brown liquid
- customThis was purified by chromatography on silica gel using 15% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-dc306c2b8cba4440b81679cf03bb421f
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04794188
Reaction notes
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