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p-Toluenesulfonic acid → (1s,3r,6r,10r)-3-(4'-Methoxyphenyl)-10-hydroxy-2,4,7-trioxabicyclo[4.4.0]decane

HRID 413609
Notes
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Reaction equation

HRID 413609 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C.[C:32]([O:35][CH2:36][CH3:37])(=O)C.C[C:39](N(C)C)=[O:40]>>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C@@H:3]2[O:12][CH2:13][C@@H:32]3[C@H:1]([C@H:39]([OH:40])[CH2:37][CH2:36][O:35]3)[O:2]2)=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 75140p-(Dimethoxymethyl)anisole

Product 1

HCID 20588607(1s,3r,6r,10r)-3-(4'-Methoxyphenyl)-10-hydroxy-2,4,7-trioxabicyclo[4.4.0]decane

Conditions

Temperature
62.5 °C

Procedure

5.0 g (33.8 mmol) of 2 and 8.30 g (45.8 mmol) of p-methoxybenzaldehyde dimethyl acetal were dissolved in 50 ml of anhydrous DMA, and a catalytic amount of 4-toluenesulfonic acid was added until the mixture was acidic. The reaction solution was agitated for about 5 hours in a rotary evaporator at 60-65° C. and a reduced pressure of 30 mbar. The reaction solution was neutralized using triethylamine. 300 ml of ethyl acetate were added, and the mixture was extracted three times with water. The organic phase was dried over Na2SO4, the drying agent was filtered off, and the residue was evaporated under reduced pressure. The crude product was dissolved in a little ethyl acetate, precipitated using n-hexane, filtered off with suction and dried under reduced pressure.

Workup

  1. extractionthe mixture was extracted three times with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationthe drying agent was filtered off
  4. customthe residue was evaporated under reduced pressure
  5. dissolutionThe crude product was dissolved in a little ethyl acetate
  6. customprecipitated
  7. filtrationfiltered off with suction
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-63a9c62168864f38bdd617b0cdcec539
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06569355B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes