Calcium Carbonate → HCID 86756225, compound

HRID 565684Notes

Reaction equation

HRID 565684 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]([CH3:11])=[CH2:10])=[C:6]([CH3:12])[C:5]([NH:13][CH:14]=[O:15])=[C:4]([CH3:16])[C:3]=1[CH3:17].C(=O)([O-])[O-].[Ca+2].I(Cl)(=O)=O.[I:27](Cl)(=O)=O.[CH2:31]([N+](C)(C)C)[C:32]1[CH:37]=CC=CC=1>O1CCCC1.CO>[I:27][CH2:10][C:9]1([CH3:11])[CH2:8][C:7]2[C:6]([CH3:12])=[C:5]([NH:13][CH:14]=[O:15])[CH:4]([CH3:16])[C:3]([CH:32]([CH3:37])[CH3:31])([CH3:17])[C:2]=2[O:1]1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 10537603HCID 10537603, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 86756225HCID 86756225, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-[4-hydroxy-2,3,6-trimethyl-5-(2-methyl-2-propenyl)phenyl]formamide (187 g) and calcium carbonate (104 g) in tetrahydrofuran (600 mL) and methanol (600 mL) was added benzyltrimethylammonium dichloroiodate (307 g) slowly. The mixture was stirred for 10 minutes. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. To the residue was added ethyl acetate (800 mL) and water (400 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic layer was washed with 10% aqueous solution hydrogen sulfite (400 g), water (300 mL), saturated aqueous sodium bicarbonate (300 mL) and aqueous sodium chloride (300 mL). The organic layer was dried over magnesium sulfate, treated with activated carbon, filtrated and the filtrate was concentrated in vacuo. The residue was crystallized from ethyl acetate/diisopropyl ether to afford 271 g of the title compound. Yield 94%.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue was added ethyl acetate (800 mL) and water (400 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (400 mL)
  6. washThe combined organic layer was washed with 10% aqueous solution hydrogen sulfite (400 g), water (300 mL), saturated aqueous sodium bicarbonate (300 mL) and aqueous sodium chloride (300 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. additiontreated with activated carbon
  9. filtrationfiltrated
  10. concentrationthe filtrate was concentrated in vacuo
  11. customThe residue was crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-934962e6dbc74a00bab7c19e1aa24a53
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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