Water → Biotin

HRID 370304Notes

Reaction equation

HRID 370304 reaction equation
C([N:8]1[C@H:22]2[C@H:11]([CH2:12][S:13][C@H:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[OH:20])[N:10](CC2C=CC=CC=2)[C:9]1=[O:30])C1C=CC=CC=1.O.S(=O)(=O)(O)O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[OH:21][C:19]([CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C@@H:22]2[C@@H:11]([NH:10][C:9]([NH:8]2)=[O:30])[CH2:12][S:13]1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 10971943HCID 10971943, compound

Product 1

HCID 171548BiotinYield 86.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

320 g of crude dibenzylbiotin (containing about 80% of pure dibenzylbiotin, 0.60 mol) are mixed with 125 g of water, and 500 g of sulfuric acid are carefully added with stirring at such a rate that the temperature of the batch does not exceed 115° C. Stirring is then continued at 115° C. for 3 hours. 2.5 l of xylene are added, and the mixture is then firstly neutralized using 5 l of 9% sodium hydroxide solution and then rendered alkaline. The aqueous phase is separated off. The xylene phase is extracted twice more with 0.5 1 of 9% sodium hydroxide solution in each case. The aqueous phase and the sodium hydroxide phases from the post-reactions are combined and adjusted to a pH of 6 at 80° C. using sulfuric acid. 12 g of activated carbon are added, the mixture is subjected to a polishing filtration, and the pH is slowly reduced to 1.5 using sulfuric acid. After the mixture has been cooled overnight, the precipitated biotin is filtered off with suction and dried, giving 128 g of biotin (content: about 99%, corresponding to 126 g of pure biotin=0.52 mol, 86% of theory).

Workup

  1. additionare carefully added
  2. customdoes not exceed 115° C
  3. stirringStirring
  4. customThe aqueous phase is separated off
  5. extractionThe xylene phase is extracted twice more with 0.5 1 of 9% sodium hydroxide solution in each case
  6. customadjusted to a pH of 6 at 80° C.
  7. addition12 g of activated carbon are added
  8. filtrationthe mixture is subjected to a polishing filtration
  9. temperatureAfter the mixture has been cooled overnight
  10. filtrationthe precipitated biotin is filtered off with suction
  11. customdried

Sources & evidence

ORD record
ord-027dd193d7f54fa186daa73373a02b30
Source dataset
uspto-grants-2000_10
Patent number
US06140507

Reaction notes

Loading…