Ethyl ketone → HCID 54502385, compound

HRID 1703530Notes

Reaction equation

HRID 1703530 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][CH3:14].[CH3:15][CH2:16][C:17](=O)[CH2:18][CH3:19]>[Pt].CCOCC.C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>[CH2:13]([C:5]1[CH:6]=[CH:7][C:8]([NH:10][CH:17]([CH2:18][CH3:19])[CH2:16][CH3:15])=[CH:9][C:4]=1[CH2:3][O:2][CH3:1])[CH3:14]

Participants

6

Reactant 2

HCID 7288Ethyl ketoneHCID 1165461-Ethyl-2-(methoxymethyl)-4-nitrobenzene

Product 1

HCID 54502385HCID 54502385, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 84202-Naphthalenesulfonic acidCatalystHCID 23939PlatinumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.0g of 2-ethyl-5-nitrobenzyl methyl ether, 10.38g of 3-pentanone, 0.23g of 2-naphthalene sulfonic acid, and 0.60g of 5% platinum on carbon catalyst was shaken under hydrogen for 2 hours at room temperature and for 4 hours at 48° C. to 60° C. The mixture was diluted with 200 ml of ether, filtered and the filtrate shaken with 2.5% aqueous sodium hydroxide, washed with water, filtered through sodium sulfate and stirred over magnesium sulfate. The filtered solution was concentrated under vacuum to yield 10.76 grams of an amber liquid, pure by glc and tlc analyses.

Workup

  1. filtrationfiltered
  2. stirringthe filtrate shaken with 2.5% aqueous sodium hydroxide
  3. washwashed with water
  4. filtrationfiltered through sodium sulfate
  5. stirringstirred over magnesium sulfate
  6. concentrationThe filtered solution was concentrated under vacuum

Sources & evidence

ORD record
ord-94336d0a36f643b6b30a62da41b0bcda
Source dataset
uspto-grants-1978_11
Patent number
US04124639

Reaction notes

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