Methanol → HCID 21288538, compound

HRID 1285483Notes

Reaction equation

HRID 1285483 reaction equation
[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#N)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C[OH:35].O>C1COCC1>[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:35])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14257786HCID 14257786, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 21288538HCID 21288538, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzonitrile (10.0 g.) in THF was added diisobutylaluminum hydride (15 g.) and the reaction was refluxed overnight. Methanol (10.2 ml) was slowly added followed by water (5.7 ml). The mixture was filtered and the filtrate was concentrated to an oil. The oil was dissolved in chloroform. The solution was washed with 5% aqueous hydrochloric acid (4 times), dried (MgSO4) and concentrated to an oil (3.0 g., 30% yield).

Workup

  1. temperaturethe reaction was refluxed overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to an oil
  4. dissolutionThe oil was dissolved in chloroform
  5. washThe solution was washed with 5% aqueous hydrochloric acid (4 times)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to an oil (3.0 g., 30% yield)

Sources & evidence

ORD record
ord-b4da3c51457d4be0bedd649bb6ee89fd
Source dataset
uspto-grants-1986_01
Patent number
US04567184

Reaction notes

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