Toluene → HCID 11995324, compound

HRID 654602Notes

Reaction equation

HRID 654602 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](C2C=CC=CC=2C(OCC)=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[O-:22][CH2:23][CH3:24].[Na+].[C:26](#[N:28])C.C1(C)C=CC=CC=1>O>[C:26]([CH2:24][C:23]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][CH:7]=1)=[O:22])#[N:28]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342AcetonitrileHCID 2723922Sodium ethoxideHCID 19887859HCID 19887859, compound

Product 1

HCID 11995324HCID 11995324, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 41.25 g. (200 mmoles) of ethyl 4-[(2-propenyl)oxy]phenylbenzoate, 15.0 g. (220 mmoles of sodium ethoxide and 13 ml. (240 mmoles) of acetonitrile in 85 ml. of dry toluene was mechanically stirred under a nitrogen atmosphere at 108° C. for 24 hours. The reaction mixture was cooled and diluted with 600 ml. of water. After all of the solid had dissolved, the mixture was washed with two 100 ml. portions of ethyl ether. The aqueous phase was then acidified to pH 5-6 with concentrated aqueous hydrochloric acid (required about 15 ml.). The precipitate which formed was collected by suction filtration, washed with water and air dried. This solid was sufficiently pure to carry directly into the next step. If desired, an analytically pure sample could be obtained by crystallization from an ethyl acetate/hexane mixture. 1H NMR (CDCl3, δ) 7.90 [d, 2H, J=9 Hz, phenyl-H(2]), 6.99 (d, 2H, J=9 Hz, phenyl-H(3)), 6.05 (m, 1H, vinyl CH), 5.43 (d, 1H, J=17 Hz, vinyl CH2), 5.35 (d, 1H, J=11 Hz, vinyl CH2), 4.63 (d, 2H, J=5 Hz, OCH2), 4,02 (s, 2H, CH2CN).

Workup

  1. additionA mixture of 41.25 g
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with 600 ml
  4. dissolutionAfter all of the solid had dissolved
  5. washthe mixture was washed with two 100 ml
  6. customThe precipitate which formed
  7. filtrationwas collected by suction filtration
  8. washwashed with water and air
  9. customdried
  10. customan analytically pure sample could be obtained by crystallization from an ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-a2c74d7455ee41789a97ed8dd3efa6b3
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

Loading…