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Chemical Structure| 155222-48-3 Chemical Structure| 155222-48-3

Structure of 155222-48-3

Chemical Structure| 155222-48-3

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Product Details of [ 155222-48-3 ]

CAS No. :155222-48-3
Formula : C12H12O4
M.W : 220.22
SMILES Code : C=CC1=CC(OC(C)=O)=CC(OC(C)=O)=C1
MDL No. :MFCD16293806

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Application In Synthesis of [ 155222-48-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 155222-48-3 ]

[ 155222-48-3 ] Synthesis Path-Downstream   1~1

  • 1
  • N,N-DMF [ No CAS ]
  • [ 35354-29-1 ]
  • [ 155222-48-3 ]
  • [ 33620-67-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; thionyl chloride;palladium diacetate; In sodium hydride; ethyl acetate; toluene; Example 41 (E)-3,3',5,5'-Tetraacetoxy-stilbene (41) Attempted preparation of the (2+2) adduct; (E)-3,5,3',5'-Tetraacetoxystilbene. Systematically named as (E)-5,5'-(ethene-1,2-diyl)bis(benzene-5,3,1-triyl) tetraacetate. 3,5-Diacetoxybenzoic acid (1.841 g, 7.735 mmol, batch BDp125-21-9-07) was suspended in sodium wire dried toluene (50 mL). Dry N,N-DMF (0.5 mL) and thionyl chloride (5.0 mL, 69 mmol) were added and the reaction was heated to reflux for three hours under an Argon gas atmosphere. All the material dissolved within 20 minutes. The solvents were removed by vacuum distillation (0.1 mm/60 C.) and the resultant yellow solid then redissolved in dry toluene (25 mL) and sonicated under vacuum for 15 minutes to remove dissolved gases. 3,5-Diacetoxystyrene (1.547 g, 7.032 mmol, batch BDp143-18-10-07), N-ethylmorpholine (983mL, 7.735 mmol) and palladium diacetate (35 mg, 0.0155 mmol, 2 mole %) were added and the mixture heated to reflux overnight under an Argon gas atmosphere. On return to room temperature, ethyl acetate (200 mL) was added and the solution washed successively with water (5*50 mL), dried (anhyd. Na2SO4), filtered and rotary evaporated to give 3.269 g of dark brown gum. TLC of this crude material showed a number of products. 1H NMR (300 MHz, CDCl3) showed no obvious trans-stilbene product, and styrene starting material. ESI mass spectroscopy suggested no penta-O-acetate or partially deacetylated adduct(s). The positive mode showed a m/z 243 [MNa+] consistent for the styrene starting material. The negative ion mode showed a m/z 237 [M-H]- consistent for the acid starting material.
 

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