Toluene → HCID 20226495, compound

HRID 1751148Notes

Reaction equation

HRID 1751148 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>O>[C:29]([O:10][CH2:9][C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:32])[CH:30]=[CH2:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 76229(1,1'-Biphenyl)-2-methanol

Product 1

HCID 20226495HCID 20226495, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 200 mL three-neck flask equipped with a stirrer, a thermometer, a cooling tube, and a calcium chloride tube, 20.0 g of ortho-phenylbenzyl alcohol, 100.0 g of anhydrous toluene, 13.2 g of triethylamine, and 7.8 mg of methoquinone were charged and cooled to 10° C. or less using an ice bath. Into the flask, 11.8 g of acryloyl chloride wad dropped for 30 minutes. The temperature was increased to room temperature and a reaction was caused to proceed for two hours. After the reaction, the reaction solution was poured into water and washed with a 5% NaOH aqueous solution and a saline solution, and the solvent was distilled off to obtain an orange liquid. The orange liquid was purified with a silica gel column to obtain 20.44 g of ortho-phenylbenzyl acrylate. The obtained ortho-phenylbenzyl acrylate was a colorless, transparent liquid at ordinary temperature and had a refractive index of 1.5776 and a viscosity of 27 mPa·s at 25° C. The measurement result of 1H-NMR is shown below.

Workup

  1. customInto a 200 mL three-neck flask equipped with a stirrer
  2. temperaturecooled to 10° C. or less
  3. customAfter the reaction
  4. washwashed with a 5% NaOH aqueous solution
  5. distillationa saline solution, and the solvent was distilled off
  6. customto obtain an orange liquid
  7. customThe orange liquid was purified with a silica gel column

Sources & evidence

ORD record
ord-a9300fe780ff40b99cebfbc0e7ecf0df
Source dataset
uspto-grants-2015_10
Patent number
US09156931B2

Reaction notes

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