Diethyl Ether → HCID 22719691, compound

HRID 228153

Reaction equation

HRID 228153 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(OCC)C.[OH-].[Na+]>ClCCl>[CH:23]1([CH2:29][CH2:30][CH2:31][CH:32]=[O:33])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 78182CyclohexanebutanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 22719691HCID 22719691, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add Dess-Martin reagent (7.02 g, 16.6 mmol) to a stirred solution of 4-cyclohexyl-1-butanol (2.5 mL, 14.4 mmol) in anhydrous dichloromethane (120 mL). Stir for 3 h at room temperature under nitrogen. Add diethyl ether (200 mL) and 1N sodium hydroxide (150 mL) and stir for 10 minutes. Separate the layers and extract a second time with diethyl ether (100 mL). Combine the diethyl ether extracts, wash with 1N sodium hydroxide (100 mL), dry over magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 2.01 g (90%) of 4-cyclohexyl-butyraldehyde: 1H NMR (CDCl3): 9.76 (s, 1H), 2.41-2.37 (m, 2H), 1.71-1.58 (m, 7H), 1.27-1.07 (m, 6H), 0.93-0.82 (m, 2H).

Workup

  1. customSeparate the layers
  2. extractionextract a second time with diethyl ether (100 mL)
  3. washwash with 1N sodium hydroxide (100 mL)
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator

Sources & evidence

ORD record
ord-c4e0824bb3e1484aa0c6dfb268f33cc6
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Linked notes

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