Diethyl Ether → 4-Methylbenzaldehyde

Reaction equation

[CH:1]1([CH2:7]C2CCCCN2CC(C2C=CC=C(Br)C=2)C)[CH2:6][CH2:5]C[CH2:3][CH2:2]1.C([Li])CCC.C([O:31][CH2:32][CH3:33])C>>[CH3:7][C:1]1[CH:6]=[CH:5][C:33]([CH:32]=[O:31])=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 128050991-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidine

HCID 178418339Butyllithium

Product 1

HCID 77254-Methylbenzaldehyde

Procedure

Following a procedure similar to that described in Example 3, 18.9 g. (0.05 mole) of 2-cyclohexylmethyl-1-[2-(3-bromophenyl)propyl]piperidine was reacted with 0.1 mole of n-butyl lithium in diethyl ether and the resulting lithio derivative reacted directly with 12.3 g. (0.103 mole) of 4-methylbenzaldehyde to give 16.9 g. of 2-cyclohexylmethyl-1-{2-[3-(α-hydroxy-4-methylbenzyl)phenyl]propyl}piperidine as a yellow oil.

Sources & evidence

ORD record: ord-f006f223293045409fda650532781a95
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04308382

Reaction notes

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