Water → HCID 13037828, compound

HRID 2413377Notes

Reaction equation

HRID 2413377 reaction equation
[CH2:1]([CH:7](O)[C:8]1[O:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.C([O-])(=[O:17])C.[Na+]>C(O)(=O)C>[CH2:1]([CH:7]1[CH:8]([OH:12])[CH:9]=[CH:10][C:11]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 10511647HCID 10511647, compound

Product 1

HCID 13037828HCID 13037828, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In an autoclave, there were charged α-n-hexylfurfuryl alcohol (I-4) (18.2 g), water (910 g) and a buffer solution (0.6 g) comprising sodium acetate and acetic acid adjusted to pH 4.7. The resultant mixture was stirred at 110° C. under a nitrogen stream. After completion of the reaction, the reaction mixture was cooled and extracted with toluene. Removal of toluene from the extract gave a mixture (15.65 g) of 2-n-hexyl-3-hydroxy-4-cyclopentenone (II-4) and 2-n-hexyl-4-hydroxy-2-cyclopentenone (III-4). Yield, 86%.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with toluene
  4. customRemoval of toluene from the extract

Sources & evidence

ORD record
ord-09b3dee6f32e474a9ad45971c985857c
Source dataset
uspto-grants-1985_01
Patent number
US04496767

Reaction notes

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