Carbon Tetrachloride → HCID 19105433, compound

HRID 248611Notes

Reaction equation

HRID 248611 reaction equation
C([CH:3]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6]C=1)=C.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[C:55]([Cl:59])(Cl)(Cl)Cl>>[CH:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:3]2[CH:4]=[CH:9][C:8]([CH2:55][Cl:59])=[CH:7][CH:6]=2)=[CH:17][CH:16]=1)=[CH2:20]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 19105436HCID 19105436, compound

Product 1

HCID 19105433HCID 19105433, compoundYield 83%

Procedure

A mixture of p-hydroxymethylbenzyl vinylbenzyl ether (39.2 g, 0.16 molar), triphenylphosphine (46.0 g, 0.18 molar), and 2,6-di-tert-butyl-p-cresol (0.5 g) in carbon tetrachloride (550 ml) was heated at reflux for 2 hours and then stirred at ambient temperature overnight. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added methanol (300 ml) to precipitate a white solid: m.p. of 110°-112° C. Yield of 83%. Analysis calculated for C16H15C10: C, 74.27, H, 5.84. Found: C, 73.15, H, 5.84, 1H NMR (CDCl3) δ 4.5 )s. 2H, CH2Cl), 5.0 (s, 2H, CH2O), 5.2+5.75 (AB quartet, 2H, CH2 =), 6.75 (m, 1H, CH=), ##STR22##

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe next day the reaction was filtered
  4. customthe solvent removed on a rotary evaporator
  5. additionTo the residue was added methanol (300 ml)
  6. customto precipitate a white solid

Sources & evidence

ORD record
ord-befeed9ee55e4e9cb09993ace7754c13
Source dataset
uspto-grants-1993_05
Patent number
US05210289

Reaction notes

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