4-Methoxybenzaldehyde → Cyclohexyl-(4-methoxyphenyl)methanol

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH:11]1([Mg]Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH:11]1([CH:7]([C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[OH:8])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Reactant 2

HCID 312444-Methoxybenzaldehyde

HCID 178419651HCID 178419651, compound

Product 1

HCID 9920862Cyclohexyl-(4-methoxyphenyl)methanol

Procedure

Referring now to FIG. 2, this alternative synthesis starts from 4-methoxy-benzaldehyde (VI) which is subjected to treatment with cyclohexyl magnesium bromide to yield cyclohexyl-(4-methoxy-phenyl)-methanol (V). This in turn is then oxidised so as to yield cyclohexyl-(4-methoxy-phenyl)-methanone (III).

Workup

customthis alternative synthesis

Sources & evidence

ORD record: ord-aacd95c11a9f4f8eb70c139deb24342e
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756502B2

Reaction notes

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