Hydrochloric Acid → 4-(Benzyloxy)-2-(hydroxyimino)-2,3-dihydro-1H-inden-1-one

HRID 1388295Notes

Reaction equation

HRID 1388295 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19](OCCC(C)C)=[O:20].Cl>CCOCC>[OH:20][N:19]=[C:12]1[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:13]1=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 136161924-(benzyloxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 714128754-(Benzyloxy)-2-(hydroxyimino)-2,3-dihydro-1H-inden-1-oneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled solution of 1.91 g (0.008 m) of 4-(phenylmethoxy)-1-indanone in 75 ml of anhydrous ether is added dropwise with stirring 1.2 ml (0.088 m) of isoamyl nitrite while hydrogen chloride is simultaneously bubbled in. After stirring at room temperature for twenty minutes, the reaction mixture is partially concentrated and the solid which separates is filtered to yield 1.83 g (86%) of material sufficiently pure to be used in the next step.

Workup

  1. additionis added dropwise
  2. customis simultaneously bubbled in
  3. concentrationthe reaction mixture is partially concentrated
  4. filtrationthe solid which separates is filtered

Sources & evidence

ORD record
ord-430e74d3c7b841a39e0c9156e5302765
Source dataset
uspto-grants-1984_02
Patent number
US04431647

Reaction notes

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