4-Hydroxybenzaldehyde → 4-Cyclohexyloxybenzaldehyde

HRID 1693976Notes

Reaction equation

HRID 1693976 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[CH:22]1(O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:22]1([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 112871794-CyclohexyloxybenzaldehydeYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (250 mL) solution of diethylazodicarboxylate (16.1 mL, 40.9 mmol) were added 4-hydroxybenzaldehyde (5 g, 40.9 mmol), cyclohexanol (4.31 mL, 40.9 mmol) and triphenylphosphine (10.7 g, 40.9 mmol). This mixture was stirred for 30 hours at room temperature. The mixture was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (2.84 g, 34%).

Workup

  1. concentrationThe mixture was concentrated under a reduced pressure
  2. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-dddd4231b23643bcbf6c0cbe55d7a846
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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