Water → 2-{2-[4-(Chloromethyl)phenyl]ethenyl}-1,4-dimethoxybenzene

HRID 2255845Notes

Reaction equation

HRID 2255845 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=1.CCOCC.O.[Cl:27]CCl>Cl>[Cl:27][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]=[CH:11][C:4]2[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 53892636HCID 53892636, compound

Product 1

HCID 545377842-{2-[4-(Chloromethyl)phenyl]ethenyl}-1,4-dimethoxybenzeneYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2,5-Dimethoxystilbene-4'-methanol (1.18 g, 4.36 mmol) in dichloromethane (3 ml) and hydrochloric acid (10M, 100 ml) was stirred for 1 h at room temperature. Ether (100 ml) and water (100 ml) were added and the organic layer separated, washed with water (2×125 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane) to give 4'-chloromethyl-2,5-dimethoxystilbene (856 mg, 68%); δH ; (CDCl3) 3.83 (3 H, s, OCH3), 3.85 (3 H, s, OCH3), 4.59 (2 H, s, CH2Cl), 6.81 (1H, dd, J=8.8, 2.7 Hz), 6.85 (1 H, d, J=8.8 Hz), 7.10 and 7.49 (2 H, d, J=16.5 Hz, vinylic H), 7.17 (1 H, d, J=2.7 Hz), 7.37 and 7.53 (4 H, AA'BB'); δc (CDCl3) 46.1, 55.7, 56.0, 111.5, 112.2, 113.6, 123.9, 126.8, 128.4, 128.7, 136.4, 137.9, 151.4 and 153.6.

Workup

  1. customthe organic layer separated
  2. washwashed with water (2×125 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography over silica (dichloromethane)

Sources & evidence

ORD record
ord-4896ea598beb4b198955ee7a7428655a
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

Loading…