Diisobutylaluminum hydride → 4-Iodo-2-propoxybenzenemethanol
Reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:12][CH2:13][CH2:14][CH3:15])[CH:3]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([O:12][CH2:13][CH2:14][CH3:15])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The procedure is the same as that described above, using 14 g of methyl 4-iodo-2-propoxybenzoate, 450 ml of toluene and 87.5 ml of DiBAlH. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 9:1 mixture. After evaporation of the solvents, 11.3 g (88%) of the expected compound are recovered in the form of a yellow oil.
Workup
- customThe product is purified by chromatography on a silica column
- washeluted with a heptane/ethyl acetate 9:1 mixture
- customAfter evaporation of the solvents, 11.3 g (88%) of the expected compound
- customare recovered in the form of a yellow oil
Sources & evidence
- ORD record
- ord-363731b29f9f4cd48a499b819f310336
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829588B2
Reaction notes
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