Water → Dibenzyl ether

HRID 439901

Reaction equation

HRID 439901 reaction equation
C([O:8][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:23])C1C=CC=CC=1.P(O)(O)O.O.[CH:29](O)(C)C>[Ir](Cl)(Cl)(Cl)Cl>[OH:23][CH:11]1[CH2:12][CH:13]([CH2:14][OH:15])[CH:10]1[CH2:9][OH:8].[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

7

Reactant 4

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

Product 2

HCID 7657Dibenzyl etherHCID 540835352,3-Bis(hydroxymethyl)cyclobutanol

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 [1α, 2β, 3β)]-3-hydroxy-1,2-cyclobutane-dimethanol, 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-2198379b9c094fa9b4d9279dd5c0e475
Source dataset
uspto-grants-1996_05
Patent number
US05516903

Linked notes

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