Diisobutylaluminum hydride → 4-Iodo-2-propoxybenzenemethanol

HRID 1171440Notes

Reaction equation

HRID 1171440 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]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68769381HCID 68769381, compound

Product 1

HCID 687684504-Iodo-2-propoxybenzenemethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. customThe product is purified by chromatography on a silica column
  2. washeluted with a heptane/ethyl acetate 9:1 mixture
  3. customAfter evaporation of the solvents, 11.3 g (88%) of the expected compound
  4. 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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