Benzene → Dibenzyl ether

HRID 482187Notes

Reaction equation

HRID 482187 reaction equation
[C:1](=[C:4]([CH:6]([CH2:8][OH:9])O)O)([CH3:3])C.[CH:10]1C=CC=C[CH:11]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([O:9][CH2:8][C:6]1[CH:4]=[CH:1][CH:3]=[CH:11][CH:10]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 7503Benzyl ChlorideHCID 9920395Isopropylideneglycerol

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Referring to FIG. 2, the preparation of 1-[12-(m-iodophenyl)-dodecyl]-2-methyl-rac-glycero-3-phosphocholine is described in detail. Isopropylidene glycerol (21.3 g, 161 mmol) was added dropwise into a flame-dried three-necked 200 ml round-bottomed flask containing anhydrous benzene (50 ml) and NaNH2 (6.62 g, 161 mmol) which was equipped with a reflux condenser. The reaction mixture was refluxed under anhydrous conditions for one hour before benzyl chloride (24.0 g, 193 mmol) was slowly added to the hot mixture. The reaction mixture was refluxed overnight. After the reaction mixture had cooled to room temperature, H2O was cautiously added. The benzene layer was removed and washed several times with H2O and dried (MgSO4). The solvent was removed in vacuo to give a dark brown oil which was purified by vacuum distillation to yield pure benzyl ether, rac-1-O-benzyl-2,3-O-isopropylidine glycerol (23.1 g, 79%).

Workup

  1. customwas equipped with a reflux condenser
  2. additionwas slowly added to the hot mixture
  3. temperatureThe reaction mixture was refluxed overnight
  4. customThe benzene layer was removed
  5. washwashed several times with H2O
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customto give a dark brown oil which
  9. distillationwas purified by vacuum distillation

Sources & evidence

ORD record
ord-b1ec6412d63842c2ad8c91ae613d0caa
Source dataset
uspto-grants-1998_08
Patent number
US05795561

Reaction notes

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