Formaldehyde → 2-(Hydroxymethyl)cyclohexanone

HRID 1703779Notes

Reaction equation

[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]=[O:9]>>[OH:9][CH2:8][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:1]1=[O:7]

Participants

Reactant 2

HCID 712Formaldehyde

HCID 7967Cyclohexanone

Product 1

HCID 214062-(Hydroxymethyl)cyclohexanone

Procedure

By condensing cyclohexanone (2) with formaldehyde, the 2-hydroxymethylcyclohexanone (3) is obtained, wherefrom, by reaction with phenylmagnesium bromide, 1-phenyl-cis-2-hydroxymethyl-r-1-cyclohexanol (4) is prepared, the latter being subsequently oxidized with potassium permanganate into the acid (1).

Sources & evidence

ORD record: ord-388057d0e1d24e30a40315e868fc397a
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125558

Reaction notes

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