Sulfuric Acid → HCID 11346391, compound

HRID 556146Notes

Reaction equation

HRID 556146 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12](O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.CC(=O)OCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 3849133HCID 3849133, compound

Product 1

HCID 11346391HCID 11346391, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the crude alcohol 2 (53 g) in toluene (500 mL) was added silica gel coated with sulfuric acid (3%, 14 g). The mixture was heated to 100° C. and monitored by TLC (prod Rf (25 EA/hex)=0.58). After three hours, the mixture was filtered. The organic phase was washed with water and sodium bicarbonate solution, dried (Na2SO4), and evaporated to give the alkene 3 (42 g, 84%) as a pale-brown solid. TLC Rf (25 EA/hex)=0.58. GC-MS Rt=13.55 min, m/z=274 (M+). 1H NMR (CDCl3, δ): 7.4-6.7 (m, 7H), 6.54 (d, J=9.6 Hz, 1H), 6.0 (m, 1H), 4.08 (t, J=8.0 Hz, 1H), 2.7 (m, 1H), 2.5 (m, 1H). 13C NMR (CDCl3, δ, mult): 143.6, 136.3, 133.8, 132.2, 130.2, 130.2, 128.1, 127.7, 127.2, 126.4, 129.7, 127.4, 42.8(1), 31.6(2).

Workup

  1. filtrationthe mixture was filtered
  2. washThe organic phase was washed with water and sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a38bfc83dcf0410d9941e5824b3d63bc
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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