Methane → Zearalanol

HRID 846324Notes

Reaction equation

HRID 846324 reaction equation
[CH2:1]1[CH2:19][CH2:18][C:17]2[C:12](=[C:13]([OH:21])[CH:14]=[C:15]([OH:20])[CH:16]=2)[C:10](=[O:11])[O:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([OH:22])[CH2:3][CH2:2]1.[C:23](#N)C.C>O>[CH3:23][C@@H:8]1[O:9][C:10](=[O:11])[C:12]2[C:17](=[CH:16][C:15]([OH:20])=[CH:14][C:13]=2[OH:21])[CH2:18][CH2:19][CH2:1][CH2:2][CH2:3][C@@H:4]([OH:22])[CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 297MethaneHCID 6342AcetonitrileHCID 101719154HCID 101719154, compound

Product 1

HCID 2999413ZearalanolYield 38.99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.59 kg of an α, β-zeranol mixture (55:45), acetonitrile with 0.5% water (80 l) and active charcoal (0.05 kg) were placed into a 150 l crystallizer. The mixture was refluxed for 30 min., warm filtered and the filtrate was refluxed again. The obtained clear solution was cooled adjusting the fall in temperature to about 8°-10° C./hour, under strong mechanic stirring, so as to obtain a controlled crystallization. Crystal withdrawals were carried out at 42° C., 36° C. and 30° C. on which crystals HPLC analysis was effected a described in Example 1: content in α-zeranol proved to be extremely constant (91.9%, 92.3% and 91.8%, respectively, at the above cited temperatures). Stirring was continued overnight and for 12 hours more at 30° C.; then the product was filtered and dried to obtain 1.40 kg (38.99%) of an α-zeranol with a 93.5% titre. This product was dissolved in 42 l of acetonitrile with 1% of water and crystallized following the same procedure as above. 1.01 kg of final product was obtained, with a 98.6% titre (HPLC), m.p.=181°-182° C., [α]D20 =46.2 (c=1.0; methanol).

Workup

  1. temperatureThe mixture was refluxed for 30 min.
  2. temperaturewarm
  3. filtrationfiltered
  4. temperaturethe filtrate was refluxed again
  5. temperatureThe obtained clear solution was cooled
  6. customunder strong mechanic stirring, so as to obtain
  7. customa controlled crystallization
  8. customwere carried out at 42° C., 36° C. and 30° C. on which crystals HPLC analysis
  9. filtrationthen the product was filtered
  10. customdried

Sources & evidence

ORD record
ord-6be7300bf2dd41a8a1bed1cba4c0a3c5
Source dataset
uspto-grants-1992_08
Patent number
US05136056

Reaction notes

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