Formaldehyde → 4,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene

HRID 462487Notes

Reaction equation

HRID 462487 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH:8]=[O:9].[CH2:10]=[O:11]>>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][C:2]2([CH2:10][OH:11])[CH2:8][OH:9]

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde

Product 1

HCID 1109174,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene

Procedure

The synthesis of this chemical compound is depicted in Table I. The synthesis consists of the reaction of cyclopentene with acrolein to produce 5-norbornene-2-al. Reaction of 5-norbornene-2-al with formaldehyde results in the formation of 5-norbornene-2,2-dimethanol. Mild oxidation of the latter compound with dibutylstannic oxide yields the 3,9-bis(5'-norbornene-2'yl)-1,5,7,11-tetraoxaspiro[5.5]undecane.

Sources & evidence

ORD record
ord-28176567ee1b4f57bad6f55744d701ad
Source dataset
uspto-grants-1985_05
Patent number
US04515912

Reaction notes

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