Water → Dibenzyl ether

HRID 36094

Reaction equation

HRID 36094 reaction equation
C(O[CH2:9][C@@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C:11]1=O)C1C=CC=CC=1.P(O)(O)O.O.[CH:29](O)(C)C>[Ir](Cl)(Cl)(Cl)Cl>[CH2:16]([O:15][CH2:14][C:13]1[CH:10]=[CH:9][CH:29]=[CH:11][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 107909Phosphorous acidHCID 14863583(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 24815Iridium tetrachlorideCatalyst

Procedure

A mixture of (2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone (0.25 g., 0.806 mmole), iridium tetrachloride (0.016 g., 0.0483 mmole), phosphorous acid (0.397 g., 4.84 mmole) and water (0.3 ml.) in isopropanol (3 ml.) was refluxed overnight. The solvent was evaporated on a rotary evaporator. The residue was taken up in ethyl acetate and washed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate. The organic layer was dried (magnesium sulfate) and the solvent was evaporated to give [1S-(1α,2β,3β)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzyl ether; TLC (40% ethyl acetate/hexane) Rf =0.51.

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated on a rotary evaporator
  3. washwashed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1ee0d42dc8654c73a17e61c3bd3a2269
Source dataset
uspto-grants-1995_05
Patent number
US05412134

Linked notes

Loading…