6-Aminohexanoic Acid → 7-Oxoheptanoic acid

HRID 564751Notes

Reaction equation

HRID 564751 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10]([O:12]C=O)C>CN(C)C=O>[CH:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:12]

Participants

4

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 8025Ethyl formate

Product 1

HCID 1697327-Oxoheptanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Aminocaproic acid (100 g, 0.76 mol) was suspended in a mixture of ethylformate and N,N-dimethylformamide (1 l, 1:1) and heated at 100° C. for 18 h. The volatiles were evaporated in vacuo and the residue treated with ethyl acetate. The solid matter was filtered off and washed with ethyl acetate and air dried which afforded 115 g (95%) of 6-formyl hexanoic acid.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. additionthe residue treated with ethyl acetate
  3. filtrationThe solid matter was filtered off
  4. washwashed with ethyl acetate and air
  5. customdried which

Sources & evidence

ORD record
ord-5152cd57acff4c15b00c2a3e4d3bf6f2
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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