Water → 2-Propenoic acid, 4-benzoylphenyl ester

HRID 231464Notes

Reaction equation

HRID 231464 reaction equation
O.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+].[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C(OCC)C>[C:19]([O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:8]=1)(=[O:22])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 962WaterHCID 13140Acryloyl chlorideHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 30151312-Propenoic acid, 4-benzoylphenyl esterYield 84.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A three-neck round-bottom flask fitted with an addition funnel, thermometer and a mechanical stirrer was charged with 100 ml of water, 40 g (0.20M) of p-hydroxybenzophenone and 8.8 g of sodium hydroxide. The flask was cooled in an ice bath to 8°-10° C., then 20 g (0.22) of acryloyl chloride were added dropwise while holding the temperature at 8°-10° C. When the addition was complete, the reaction mixture was stirred for an additional half hour. Then 150 ml of diethyl ether was added to dissolve the product of the reaction. The ether layer was separated from the water layer and washed twice with 3% sodium hydroxide and twice with water. The solution was dried over magnesium sulfate, filtered and stripped. An amount of 43.0 g of an oily product was obtained and purified by recrystallization from absolute ethanol, from which an amount of about 34.7 g of white crystalline product was isolated.

Workup

  1. customA three-neck round-bottom flask fitted with an addition funnel
  2. temperatureThe flask was cooled in an ice bath to 8°-10° C.
  3. customat 8°-10° C
  4. additionWhen the addition
  5. dissolutionto dissolve
  6. customthe product of the reaction
  7. customThe ether layer was separated from the water layer
  8. washwashed twice with 3% sodium hydroxide and twice with water
  9. dry with materialThe solution was dried over magnesium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-e035063af6d549b98bfc9d64e8274226
Source dataset
uspto-grants-1989_07
Patent number
US04847137

Reaction notes

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