Carbon Dioxide → HCID 20226493, compound

HRID 1404320Notes

Reaction equation

HRID 1404320 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]([OH:25])(=[O:24])[CH:22]=[CH2:23].C(=O)=O>CN(C)C=O>[C:21]([O:25][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:4]=1)(=[O:24])[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 6581Acrylic AcidHCID 11430Potassium CarbonateHCID 38644053-(Bromomethyl)biphenyl

Product 1

HCID 20226493HCID 20226493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 200 mL four-neck flask equipped with a stirrer, a thermometer, and a cooling tube, 20.0 g of 3-(bromomethyl)biphenyl, 39.3 g of anhydrous dimethylformamide, 13.4 g of anhydrous potassium carbonate, and 6.2 mg of methoquinone were charged, and acrylic acid was added thereto at room temperature. After the completion of foaming of carbon dioxide, the mixture was heated to a reaction temperature of 90° C. and a reaction was caused to proceed for two hours. The temperature was decreased to room temperature, and then dilution with 120 mL of water, extraction with 100 g of toluene, and washing with water were performed. The resultant crude reaction product was purified with a silica gel column to obtain 16.1 g of meta-phenylbenzyl acrylate. The obtained meta-phenylbenzyl acrylate was a colorless, transparent liquid at ordinary temperature and had a refractive index of 1.5888 and a viscosity of 24 mPa·s at 25° C. The measurement result of 1H-NMR is shown below.

Workup

  1. customInto a 200 mL four-neck flask equipped with a stirrer
  2. customat room temperature
  3. customwas decreased to room temperature
  4. extractiondilution with 120 mL of water, extraction with 100 g of toluene
  5. washwashing with water
  6. customThe resultant crude reaction product
  7. customwas purified with a silica gel column

Sources & evidence

ORD record
ord-2472b08f0a634820876d6a709ffae94f
Source dataset
uspto-grants-2014_12
Patent number
US08912300B2

Reaction notes

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