4-Nitrobenzyl alcohol → HCID 14010502, compound

HRID 1905096Notes

Reaction equation

HRID 1905096 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:12]=[C:13]([CH2:20][CH3:21])[CH2:14][C:15](OCC)=[O:16]>C1(C)C=CC=CC=1>[O:12]=[C:13]([CH2:20][CH3:21])[CH2:14][C:15]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)=[O:16]

Participants

4

Reactant 2

HCID 692754-Nitrobenzyl alcoholHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 14010502HCID 14010502, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 55.3 g (0.36 mole) of 4-nitrobenzyl alcohol and 56.2 g (0.39 mole) of ethyl 3-oxopentanoate in 360 ml of toluene was heated to boiling. About 300 ml of toluene were distilled out over the course of 10 h, then the mixture was cooled and another 200 ml were added and this procedure was repeated. After cooling, the mixture was filtered through kieselguhr, which was washed with toluene, and the filtrate solution was evaporated in vacuo. 89 g (98%) of the title compound were obtained as an oil, Rf: 0.42 (toluene:ethyl acetate 4:1).

Workup

  1. temperaturewas heated to boiling
  2. distillationAbout 300 ml of toluene were distilled out over the course of 10 h
  3. temperaturethe mixture was cooled
  4. additionanother 200 ml were added
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered through kieselguhr, which
  7. washwas washed with toluene
  8. customthe filtrate solution was evaporated in vacuo

Sources & evidence

ORD record
ord-fa34b5d06ccf47f8814f53529058d996
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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