Water → Idebenone

HRID 1905347Notes

Reaction equation

HRID 1905347 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].C([O-])(=[O:26])C.[Na+].O.N(S([O-])(=O)=O)(S(O)(=O)=O)O.[K+].[K+]>CO>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:3]1[C:2](=[O:1])[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[C:5](=[O:26])[C:4]=1[CH3:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 517045Sodium AcetateHCID 128241262-(10-Hydroxydecyl)-5,6-dimethoxy-3-methylphenolHCID 101073955dipotassium;N-hydroxy-N-sulfosulfamate

Product 1

HCID 3686IdebenoneYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (110 l) was dissolved 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decan-1-ol (6.84 kg). To this solution were added sodium acetate (27.4 kg) and water (110 l). To the mixture was then added dipotassium nitrosodisulfonate (23.5 kg, content 69.9%), which was stirred at 50°±3° C. for 3 hours. After confirming disappearance of the starting material by means of thin-layer chromatography, water (550 l) was added to the mixture, which was stirred at 10° C. or below for 30 minutes or longer, then precipitating crystals were separated by centrifuge. Wet crystals thus collected were dissolved in ethyl acetate (40 l), followed by washing with water (25). The ethyl acetate layer was concentrated under reduced pressure to obtain a crude product 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (6.70 kg, yield 93.9%). Reference examples using dipotassium nitrosodisulfonate (Fremy's salt) are described in Table 3.

Workup

  1. additionwas added to the mixture, which
  2. customprecipitating crystals
  3. customwere separated by centrifuge
  4. customWet crystals thus collected
  5. dissolutionwere dissolved in ethyl acetate (40 l)
  6. washby washing with water (25)
  7. concentrationThe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a10c9ae22e24587bcb5820be84a15e6
Source dataset
uspto-grants-1989_06
Patent number
US04842775

Reaction notes

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