Ammonia → HCID 131723472, compound

HRID 1278531Notes

Reaction equation

HRID 1278531 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]12([CH3:18])[C:14]([CH3:16])([CH3:15])[CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]2[OH:17].[Al].N.COC1C=CC(C=O)=CC=1.S(=O)(=O)(O)O>CN(C)C1C=CN=CC=1.O.C(O)(=O)C.CO.C(OCC)(=O)C.N1C=CC=CC=1>[C:1]([OH:6])(=[O:7])[CH2:2][CH2:3][C:4]([OH:17])=[O:5].[C:8]12([CH3:18])[C:14]([CH3:15])([CH3:16])[CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]2[OH:17].[C:8]12([CH3:18])[C:14]([CH3:15])([CH3:16])[CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]2[OH:17]

Participants

13

Reactant 6

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 7922Succinic anhydrideHCID 312444-MethoxybenzaldehydeHCID 64685BorneolHCID 5359268Aluminum

Product 1

HCID 131723472HCID 131723472, compound

Reagents, catalysts & solvents 6

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

First, 4-(dimethyl amino) pyridine (31.1 mg) was added to 9.1 ml pyridine, before adding succinic anhydride (487.7 mg). Borneol (168.4 mg) was added last, and the reaction mixture was heated under reflux with stirring for 53 hr at 65° C. The reaction was monitored by thin layer chromatography (“TLC”). The TLC assay used silica gel 60 F264 aluminum sheets (0.2 mm thick) from E. Merck (Darmstadt, Germany) with a mobile phase of 100 % ethyl acetate, 100% methanol, and 1% aqueous ammonia in a ratio of 80:20:1. The resulting bands were visualized by adding a mixture of 100% anisaldehyde, 100% acetic acid, and 100% sulfuric acid in a ratio of 0.5:50:1. The reaction was stopped with 20 ml H2O. The resultant product was extracted three times, each time with 25 ml methylene chloride. The organic layer was collected from each extract, pooled, rotaevaporated to dryness, and then dried under vacuum in the presence of phosphorous pentoxide. The product produced was boreol-hemisuccinate.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux
  3. additionby adding
  4. extractionThe resultant product was extracted three times
  5. customThe organic layer was collected from each extract
  6. dry with materialdried under vacuum in the presence of phosphorous pentoxide
  7. customThe product produced

Sources & evidence

ORD record
ord-a97c373222484660818d93ce6e0637d5
Source dataset
uspto-grants-2002_09
Patent number
US06444433B1

Reaction notes

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