4-Hydroxybenzaldehyde → 4-(Cyclopentyloxy)benzaldehyde

HRID 1691126Notes

Reaction equation

HRID 1691126 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)[CH2:26][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)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 31527244-(Cyclopentyloxy)benzaldehydeYield 56%

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), cyclopentanol (3.71 mL, 40.9 mmol) and triphenylphosphine (10.7 g, 40.9 mmol). This mixture was stirred for 30 minutes 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 (4.36 g, 56%).

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-a06ad92dcdc841f7908c8d7f9be7ec55
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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