Ethanol → 1-(4-(4-Hydroxy-3-(hydroxymethyl)-3-nitrobutyl)phenyl)octan-1-one

HRID 1028880Notes

Reaction equation

HRID 1028880 reaction equation
[CH2:1]=[O:2].[N+:3]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=1)([O-:5])=[O:4].[CH2:24]([OH:26])C>>[OH:2][CH2:1][C:6]([CH2:24][OH:26])([N+:3]([O-:5])=[O:4])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 569671461-(4-(3-Nitropropyl)phenyl)octan-1-one

Product 1

HCID 866938121-(4-(4-Hydroxy-3-(hydroxymethyl)-3-nitrobutyl)phenyl)octan-1-one

Procedure

Compound (18) was prepared by Henry addition of formaldehyde (37% aqueous solution) to 1-(4-(3-nitropropyl)phenyl)octan-1-one (17) in ethanol, in the presence of strongly basic anion exchange resin Amberlite IRA-401(0H-), according to the procedure described by Astle and Abbot [J. Org. Chem. 21, 1228 (1956)]. The yield of the desired product was 65%.

Sources & evidence

ORD record
ord-218961929bac4e81ab10242270e043c7
Source dataset
uspto-grants-2014_05
Patent number
US08735627B2

Reaction notes

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