Benzaldehyde → HCID 83488927, compound

HRID 1402816Notes

Reaction equation

HRID 1402816 reaction equation
BrC1C=CC=CC=1C=O.C([O-])(=O)CC(C)=O.C(=O)C1C=CC=CC=1.[OH-].[Na+].Cl.[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]([CH2:40][C:41]([OH:43])=[O:42])[CH2:36][C:37]([OH:39])=O>C(OCC)(=O)CC(C)=O.C(O)C.C(Cl)(=O)C>[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]1[CH2:36][C:37](=[O:39])[O:43][C:41](=[O:42])[CH2:40]1

Participants

10

Reactant 6

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 811292-BromobenzaldehydeHCID 6971017AcetoacetateHCID 667600413-(2-Bromophenyl)pentanedioic acid

Product 1

HCID 83488927HCID 83488927, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6367Acetyl chlorideSolventHCID 8868Ethyl AcetoacetateSolvent

Procedure

To a solution of commercial 2-bromobenzaldehyde (5 g) in ethyl acetoacetate (7 g) piperidine (0.5 ml) was added with stirring at rt. The cloudy solution was kept at rt for 3 d. The yellowish amorphous solid (the bis-adduct of acetoacetate to the benzaldehyde) was dissolved in ethanol (20 ml). This solution was added in portions to 40% NaOH (150 g) with stirring. The resulting orange slurry was stirred at reflux for 2 h. After cooling in an ice bath the now yellowish mixture was acidified by portionwise addition of conc. HCl (150 ml) to give a white, partly resinous precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-(2-bromophenyl)glutaric acid (5.7 g) was obtained. The suspension of finely divided 3-(2-bromophenyl)glutaric acid in acetyl chloride (7 ml) was heated to reflux with stirring for 1 h. After cooling to rt precipitation was induced by addition of petrol ether (50 ml). From the oily precipitate the mother liquor was removed by decantation and the residue was dried in vacuo to afford 3-(2-bromophenyl)glutaric anhydride (4.6 g) as light yellow solid in sufficient purity.

Workup

  1. stirringwith stirring
  2. stirringThe resulting orange slurry was stirred
  3. temperatureat reflux for 2 h
  4. temperatureAfter cooling in an ice bath the now yellowish mixture
  5. customto give a white, partly resinous precipitate
  6. filtrationThe solid was collected by suction filtration
  7. washwashed with water
  8. dry with materialAfter drying in vacuo 3-(2-bromophenyl)glutaric acid (5.7 g)
  9. customwas obtained
  10. temperaturewas heated
  11. temperatureto reflux
  12. stirringwith stirring for 1 h
  13. temperatureAfter cooling to rt
  14. customprecipitation
  15. additionwas induced by addition of petrol ether (50 ml)
  16. customFrom the oily precipitate the mother liquor was removed by decantation
  17. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-42d14360492c439a8499e6961f8633dc
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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