Acetic Acid → 6-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

HRID 218242Notes

Reaction equation

HRID 218242 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]\[C:15]2[C:20]([O:21][Si](C(C)(C)C)(C)C)=[C:19]([O:29][Si](C(C)(C)C)(C)C)[CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]\[C:15]2[C:20]([OH:21])=[C:19]([OH:29])[CH:18]=[CH:17][CH:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 601306896-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy) benzene

Product 1

HCID 99721426-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-dihydroxybenzeneYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8 (0.106 g, 0.2 mmol) in 2 mL THF was stirred at 0° while adding acetic acid (0.024 g, 0.4 mmol) and tetrabutylammonium fluoride (1M in THF, 0.4 ml, 0.4 mmol). The solution was stirred at 20° for one hour then cooled to 0° and 0.5 mL water added. The mixture was extracted with TBME three times, dried, evaporated and the residue partitioned between 10 mL heptane/10 mL acetonitrile. Evaporation of the acetonitrile layer gave 0.057 g pale yellow gum which was purified by silica chromatography with 7:3 heptane:ethyl acetate to give ZSB-82 as a colourless gum (0.032 g):

Workup

  1. temperaturethen cooled to 0°
  2. extractionThe mixture was extracted with TBME three times
  3. customdried
  4. customevaporated
  5. customthe residue partitioned between 10 mL heptane/10 mL acetonitrile
  6. customEvaporation of the acetonitrile layer

Sources & evidence

ORD record
ord-6a871dd083a145b58d35addf9de6b527
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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