Hydrochloric Acid → HCID 235708, compound

HRID 1003186Notes

Reaction equation

HRID 1003186 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.C=O.[CH3:23][N:24]([CH2:26]N(C)C)[CH3:25].Cl>CCO.C1C=CC=CC=1>[CH3:23][N:24]([CH2:26][C:8]1[C:9]([OH:20])=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:5]([C:6]=2[CH:7]=1)[CH2:4][CH2:3][C@@:2]1([CH3:1])[C@H:15]3[CH2:16][CH2:17][C:18]1=[O:19])[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 5870Estrone

Product 1

HCID 235708HCID 235708, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of estrone (11, 5.40 g, 20 mmol) in EtOH (100 mL) and benzene (60 mL) were added paraformaldehyde (0.600 g, 20 mmol) and N,N,N',N'-tetramethyldiaminomethane (5.5 mL, 40 mmol), and stirred for 20 h at 80° C. After the reaction mixture was cooled to 0° C., 5 N HCl was added. The aqueous layer was washed with Et2O, and basified with aqueous NH4OH. The precipitate was collected by filtration and washed with H2O, and recrystallized from EtOH to afford 4.37 g of 72 (67% yield) mp: 172-173° C.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. washThe aqueous layer was washed with Et2O
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-493852095fce43409f09dd313e818dae
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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