Acetic Acid → 4,4'-dimethoxystilbene

HRID 1449290Notes

Reaction equation

HRID 1449290 reaction equation
[C:1]([O-])(=[O:3])C.[Na+].CO[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)CBr)=[CH:10][CH:9]=1.[C:25](O)(=O)C>>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH:14]=[CH:11][C:10]2[CH:9]=[CH:8][C:13]([O:3][CH3:1])=[CH:12][CH:25]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1884691-(2-Bromo-1-(4-methoxyphenyl)ethyl)-4-methoxybenzeneHCID 517045Sodium Acetate

Product 1

HCID 208284,4'-dimethoxystilbeneYield 69.4%

Conditions

Temperature
190 °C

Procedure

The Parr bomb described in EXAMPLE 6 above was employed. To a solution of 20.0 grams (0.24 mole) of anhydrous sodium acetate dissolved in 200 milliliters of glacial acetic acid was added the entire crude 1,1-bis(4-methoxyphenyl)-2-bromoethane (66.0 grams, 0.21 mole based on pure product) from EXAMPLE 8 above. The bomb was flushed and then pressurized to 110 psig with dry nitrogen. The contents were heated, with stirring, to 190° C. over a 30-minute period, maintained at that temperature for 1 hour, and allowed to cool over a 2-hour period. The solid which crystallized was collected by suction filtration, washed successively with 50 milliliters of acetic acid, followed by 300 milliliters of warm water in a beaker. The crystalline material was collected and dried under vacuum to yield 33.3 grams (69.4 percent based on bromoacetal employed in EXAMPLE 8 above) of 4,4'-dimethoxystilbene.

Workup

  1. customThe bomb was flushed
  2. temperatureThe contents were heated
  3. temperaturemaintained at that temperature for 1 hour
  4. temperatureto cool over a 2-hour period
  5. customThe solid which crystallized
  6. filtrationwas collected by suction filtration
  7. washwashed successively with 50 milliliters of acetic acid
  8. customThe crystalline material was collected
  9. customdried under vacuum

Sources & evidence

ORD record
ord-8ead2bd339674a109555a7e283b2ef5f
Source dataset
uspto-grants-1980_02
Patent number
US04189610

Reaction notes

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