Potassium sodium tartarate → [2-(Benzyloxy)-5-iodophenyl]methanol

HRID 269594Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:20]=1[CH:21]=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>ClCCl>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:20]=1[CH2:21][OH:22])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

100 ml of a 1M diisobutylaluminum hydride solution in dichloromethane are added to a solution, cooled to 0° C., of 33.98 g (100.5 mmol) of 2-benzyloxy-5-iodobenzaldehyde (Example 2A) in 200 ml of dichloromethane. After stirring at 0° C. for 2 h, a saturated potassium sodium tartrate solution is added while cooling (highly exothermic reaction), and the reaction mixture is stirred for a further 2 h. After the separation of the phases, the organic phase is washed twice with water and once with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent is evaporated in vacuo. 31.8 g (93% of theory) of product are obtained.

Workup

temperaturewhile cooling (
customhighly exothermic reaction), and the reaction mixture
stirringis stirred for a further 2 h
customAfter the separation of the phases
washthe organic phase is washed twice with water and once with a saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
customThe solvent is evaporated in vacuo
custom31.8 g (93% of theory) of product are obtained

Sources & evidence

ORD record: ord-7bcd6824560e4b9c9644522f7863956a
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446102B2

Reaction notes

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