Sulfuric Acid → HCID 16061293, compound

HRID 1457507Notes

Reaction equation

HRID 1457507 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:42])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:41])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[CH:23]=[CH:24]/[CH:25]=[C:26](/[CH:28]=[CH:29]/[CH:30]=[C:31](/[CH:33]=[CH:34]/[C:35]([C:37]([OH:40])([CH3:39])[CH3:38])=[O:36])\[CH3:32])\[CH3:27])\[CH3:22].[Na].S(=O)(=O)(O)O>C(Cl)Cl.CO>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:42])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:41])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[CH:23]=[CH:24]/[CH:25]=[C:26](/[CH:28]=[CH:29]/[CH:30]=[C:31](/[CH:33]=[CH:34]/[C@@H:35]([OH:36])[C:37]([OH:40])([CH3:39])[CH3:38])\[CH3:32])\[CH3:27])\[CH3:22]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 5360545SodiumHCID 87443362β,ψ-Carotene, 3′,4′-didehydro-1′,2′-dihydro-1′-hydroxy-2′-oxo-

Product 1

HCID 16061293HCID 16061293, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

70.0 g (123 mmol) of 2'-dehydroplectaniaxanthin are dissolved in 2000 ml of methylene chloride and 500 ml of methanol. At 16-18° C. 4.70 g (123 mmol) of sodium borohyride are added in portions, and the mixture is stirred for 1.5 hours at room temperature. The resulting solution is then cooled to 10° C., and approx. 150 ml of 1N sulphuric acid are added at such a rate that the temperature is maintained between 10° and 15° C. until a pH between 7 and 8 is obtained. The resulting mixture is then extracted three times with 500 ml of methylene chloride in each case. The organic layer is washed several times with 500 ml of ice-water, then dried over anhydrous sodium sulphate and evaporated at 35° C. using a water jet vacuum. The resulting crystalline mass is stirred with 1500 ml of diethyl ether and the resulting suspension filtered. In this way there are obtained 12.2 g (HPLC purity 97%) of racemic plectaniaxanthin crystals.

Workup

  1. customAt 16-18° C
  2. temperatureThe resulting solution is then cooled to 10° C.
  3. temperatureis maintained between 10° and 15° C. until a pH between 7 and 8
  4. customis obtained
  5. extractionThe resulting mixture is then extracted three times with 500 ml of methylene chloride in each case
  6. washThe organic layer is washed several times with 500 ml of ice-water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated at 35° C.
  9. stirringThe resulting crystalline mass is stirred with 1500 ml of diethyl ether
  10. filtrationthe resulting suspension filtered

Sources & evidence

ORD record
ord-0cf02fa20a0f4cb28295c40b36d6faf2
Source dataset
uspto-grants-1998_12
Patent number
US05849345

Reaction notes

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