Sodium Dithionite → HCID 19900610, compound

HRID 1029991Notes

Reaction equation

HRID 1029991 reaction equation
[C:1](=[O:40])([O:9][C:10]1[C:11]([CH3:39])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:38])([CH2:22][CH2:23][CH2:24][CH:25]([CH3:37])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:14][CH2:13]2)[O:2][CH2:3][CH:4]=[C:5]([CH3:8])[CH2:6][OH:7].ClC1C=CC=C(C(OO)=[O:49])C=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[C:1](=[O:40])([O:9][C:10]1[C:11]([CH3:39])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:38])([CH2:22][CH2:23][CH2:24][CH:25]([CH3:37])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:14][CH2:13]2)[O:2][CH2:3][CH:4]1[O:49][C:5]1([CH3:8])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 53663003HCID 53663003, compound

Product 1

HCID 19900610HCID 19900610, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.1 g (0.0073 mol) of 4-hydroxy-3-methyl-2-butenyl 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanyl carbonate was dissolved in 80 ml of dichloromethane. To the obtained solution was added 2.6 g (0.012 mol) of m-chloroperbenzoic acid (purity: 80%) in small portions under ice-cooling and stirring. After the completion of the addition, the obtained mixture was further stirred at the same temperature for 1 hour. After filtering off the precipitate thus formed, the filtrate was poured into an aqueous solution of sodium hydrosulfite and extracted with dichloromethane. The extract was washed with water and dried. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, hexane/ethyl acetate). Thus 4.0 g of the title compound was obtained as a colorless viscous liquid.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. stirringthe obtained mixture was further stirred at the same temperature for 1 hour
  4. filtrationAfter filtering off the precipitate
  5. customthus formed
  6. extractionextracted with dichloromethane
  7. washThe extract was washed with water
  8. customdried
  9. distillationAfter distilling off the solvent
  10. customthe obtained oily residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3acecc6cb3de4d0885cb75ca98871a1d
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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