Nitrite → 9,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde

HRID 442514Notes

Reaction equation

N[C:2]12[CH:17]([OH:18])[CH2:16][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=31)[C:8]1[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=1.N(O)=O.N([O-])=O>>[CH:17]([C:2]12[CH2:16][CH:9]([C:8]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=31)[C:10]1[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

Reactant 3

HCID 946Nitrite

HCID 24529Nitrous Acid

HCID 124041369-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene

Product 1

HCID 124041419,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde

Procedure

9-Formyl-9,10-dihydro-9,10-methanoanthracene (iii) is prepared from 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (ii) by treatment with nitrous acid or metal nitrite in an acidic medium.

Sources & evidence

ORD record: ord-9984147bf45f426d85666484f730414f
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04045560

Reaction notes

Loading…