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Triacetoxyperiodinane → 4-Benzyloxymethyl-cyclohexanecarbaldehyde

HRID 2091989
Notes
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Reaction equation

HRID 2091989 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

Product 1

HCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane 28 mL is added Dess-Martin periodinate (2.53 g, 6 mmol) at 0° C., and the mixture is stirred for 0.5 hour while warming to room temperature. After addition of saturated aqueous NaHCO3, the mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain 4-benzyloxymethyl-cyclohexanecarbaldehyde as clear oil (1.07 g, 79%) after purification.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe combined organic layer after dried over MgSO4
  3. concentrationis concentrated

Sources & evidence

ORD record
ord-2d2a48d81fa04660ad764f402b77610d
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440682B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes