Water → HCID 131710942, compound

HRID 973098Notes

Reaction equation

HRID 973098 reaction equation
O.S(=O)(=O)(O)O.[C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]1[CH:20]([CH:21]=[O:22])[CH2:19][CH2:18][C:17]1=[O:23])([OH:9])=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.C[C:36](C)=[O:37].[CH3:39]CCCCC>[OH-].[Na+].CO.CCOCC>[CH3:39][O:23][C:17]1([O:37][CH3:36])[CH2:18][CH2:19][CH:20]([CH:21]=[O:22])[CH:16]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]([OH:9])=[O:8]

Participants

9

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 12719290HCID 12719290, compoundHCID 21880519Acetone hexane

Product 1

HCID 131710942HCID 131710942, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-(6-carboxyhexyl)-3-nitromethylcyclopentan-1-one methyl ester (20 g) in sodium hydroxide (10%, 61.6 ml) and methanol (40 ml) is stirred overnight, dilited with water (140 ml), and added to a mixture of concentrated sulfuric acid (18.4 ml) and water (118 ml) maintained -5° to -10° . A small amount of ether is added to keep the compound well suspended in the liquid. After completion of addition the cooling bath is removed and the mixture is stirred for 1 hour, extracted with ether, washed, dried and evaporated under reduced pressure to give a residue containing 2-(6-carboxyhexyl)cyclopentan-1-on-3-al γmaxFilm 2700, 1730 cm-1. This residue is refluxed in methanol (120 ml) containing p-toluenesulfonic acid (3 g) for 1.5 to 2 hours, the solvent evaporated, and the residue extracted with ether, washed with water, dried and evaporated to yield a residue which is passed through silica gel (1 kg) in 20% acetone-hexane to yield the methyl ester of 2-(6-carboxyhexyl)cyclopentan-1-on-3-al dimethyl acetal γmaxFilm 1730, 1124, 1072 cm-1NMR: (CDCl3) 4.25, 3.63, 3.38δ.

Workup

  1. temperaturemaintained -5° to -10°
  2. additionAfter completion of addition the cooling bath
  3. customis removed
  4. extractionextracted with ether
  5. washwashed
  6. customdried
  7. customevaporated under reduced pressure
  8. customto give a residue
  9. customthe solvent evaporated
  10. extractionthe residue extracted with ether
  11. washwashed with water
  12. customdried
  13. customevaporated
  14. customto yield a residue which

Sources & evidence

ORD record
ord-a650eacd35664082833a98e2ee14ab6d
Source dataset
uspto-grants-1977_10
Patent number
US04054741

Reaction notes

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