Water → HCID 10752540, compound

HRID 1032251Notes

Reaction equation

HRID 1032251 reaction equation
O[CH:2]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[OH2:18]>P(=O)(O)(O)O.P([O-])([O-])(O)=O.[K+].[K+]>[OH:14][CH:15]1[CH:16]=[CH:17][C:13](=[O:18])[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 962WaterHCID 10728746HCID 10728746, compound

Product 1

HCID 10752540HCID 10752540, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 22644153HCID 22644153, compoundCatalyst

Procedure

Into a four necked-flask equipped with a stirrer and a thermometer, 2-(1-hydroxy-7-methoxycarbonylheptyl)-furan 114 g), water (4560 g) and potassium monohydrogen phosphate-phosphoric acid buffer (3.8 g) were charged, and the resulting mixture (pH 4.2) was stirred at 100° C. under nitrogen stream until the starting compound was consumed perfectly. The reaction mixture was cooled and extracted with methylisobutylketone (600 ml) two times. The extracts were combined together and concentrated under reduced pressure to give a mixture (92 g) of 3-hydroxy-2-(6-methoxycarbonylhexyl)-4-cyclopentenone and 4-hydroxy-2-(6-methoxycarbonylhexyl)-2-cyclopentenone. Yield, 80.7%.

Workup

  1. customInto a four necked-flask equipped with a stirrer
  2. customwas consumed perfectly
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with methylisobutylketone (600 ml) two times
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96de01cd7656405ca2128f25403a97c5
Source dataset
uspto-grants-1990_09
Patent number
US04957867

Reaction notes

Loading…