Hydrochloric Acid → HCID 54281005, compound

HRID 2255843Notes

Reaction equation

HRID 2255843 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][C:4]=1[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1.Cl.[Cl:24]CCl>O1CCOCC1>[C:19]([C:16]1[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[C:4]([CH:15]=1)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Cl:24])=[CH:9][CH:8]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 53817195HCID 53817195, compound

Product 1

HCID 54281005HCID 54281005, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2'-methoxy-5'-tert-butylstilbene-4-methanol (5.83 g, 19.7 mmol) in 1,4-dioxane (25 ml) was poured into concd. hydrochloric acid (120 ml). A colourless precipitate appeared immediately. The mixture was stirred for 1 h. Then dichloromethane (250 ml) was added. The organic layer was washed with water (500 ml), brine (250 ml), dried over anhydrous magnesium sulfate, filtered and concentrated vacuo. The residue was purified by column chromatography over silica (dichloromethane) and by recrystallisation from hot hexane to yield (19) (4.26 g, 69%) in form of colourless crystals, m.p. 103°-104° C.; (Found: C, 76.42; H, 7.42. C20H24ClO requires C, 76.30; H, 7.36%); δH (CDCl3) 1.40 (9 H, s, tert-butyl), 3.90 (3 H, s, OCH3), 4.62 (2 H, s, CH2Cl), 6.88 (1 H, d, J=8.7 Hz, Phil), 7.17 (1 H, d, J=16.5 Hz, vinylic H), 7.32 (1 H, dd, J=8.6, 2.5 Hz, PhH), 7.40 and 7.57 (4 H, AA'BB', PhH), 7.54 (1 H, d, J=16.0 Hz, vinylic H), 7.65 (1 H, d, J=2.4 Hz, PhH); m/z 316, 314 (35, M+), 301, 299 (29, 91%).

Workup

  1. washThe organic layer was washed with water (500 ml), brine (250 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated vacuo
  5. customThe residue was purified by column chromatography over silica (dichloromethane) and by recrystallisation from hot hexane

Sources & evidence

ORD record
ord-2191159bb81f4fcd9b1461cc5b411893
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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