Hydroxyamine hydrochloride → 6-Benzyloxy-2,2-dimethylchroman-4-one oxime

HRID 567055

Reaction equation

HRID 567055 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23][OH:24]>C(O)C.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]2=[N:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 117809926-Benzyloxy-2,2-dimethylchroman-4-one

Product 1

HCID 867545186-Benzyloxy-2,2-dimethylchroman-4-one oximeYield 105.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

By heating 11.3 g (40 mmol) of 6-benzyloxy-2,2-dimethylchroman-4-one with 3.1 g (44 mmol) of hydroxylamine hydrochloride in 27 ml of ethanol and 27 ml of pyridine to 70° C. for 3 h, 12.5 g of product, m.p. 105-108° C., were obtained after distilling off the solvt in vac. and precipitating with water. The product was dissolved in EA, dried, concentrated and crystallized using petroleum ether; m.p. 118-120° C.

Sources & evidence

ORD record
ord-68c0d3342c694d63bf6284eaafb700be
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Linked notes

Loading…