Ammonium Chloride → Dimethyl 4,4'-[2-(hydroxymethyl)butane-1,4-diyl]dibenzoate

HRID 1512205Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[C:11](O)=[O:12])=[CH:7][CH:6]=1)=[O:4].[Cl-].[NH4+]>C1COCC1.O.C(OCC)(=O)C>[OH:12][CH2:11][CH:10]([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:21]=1)[CH2:9][C:8]1[CH:26]=[CH:27][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At −10° C., 112.8 ml (112.8 mmol) of a 1 M borane/THF complex solution are added dropwise to a solution of 20.9 g (56.4 mmol) of 2-[4-(methoxycarbonyl)benzyl]-4-[4-(methoxycarbonyl)-phenyl]butanoic acid in 600 ml of THF. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 4 h. After the reaction has gone to completion, saturated ammonium chloride solution is added, the reaction mixture is diluted with water and ethyl acetate, the phases are separated and the aqueous phase is re-extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and, after filtration, freed from the solvent under reduced pressure. This gives 20.11 g (purity 94%, 100% of theory) of a colorless solid.

Workup

additionis added
customthe phases are separated
extractionthe aqueous phase is re-extracted twice with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
filtrationafter filtration

Sources & evidence

ORD record: ord-dd800ee560c54966a1b0f1e0456c270d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

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