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

HRID 1913792Notes

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

112.8 ml (112.8 mmol) of a 1 M boran-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 at −10° C. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 4 h. After reaction is complete, saturated ammonium chloride solution is added to the reaction mixture, which is diluted with water and ethyl acetate, the phases are separated, and the aqueous phase is back-extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and, after filtration, freed of solvent in vacuo. 20.11 g (94% purity, 100% of theory) of a colourless solid are obtained.

Workup

customAfter reaction
customthe phases are separated
extractionthe aqueous phase is back-extracted twice with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulphate
filtrationafter filtration
custom20.11 g (94% purity, 100% of theory) of a colourless solid are obtained

Sources & evidence

ORD record: ord-e74a99c5d1b94a549c7698d41830bdc8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

Loading…