Bromocyclopentane → 3-Cyclopentoxy-4-nitrobenzyl alcohol

HRID 1073740

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[N+:10]([O-:12])=[O:11])[CH2:5][OH:6])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 9.6 g (56.5 mmol) of 3-hydroxy-4-nitrobenzyl alcohol in 960 mL of dry N,N-dimethylformamide under a nitrogen atmosphere was added 11.7 g (83.6 mmol) of anhydrous potassium carbonate followed by 18.1 mL (169.0 mmol) of cyclopentyl bromide. The reaction mixture was warmed to 50° C. for 24 hours after which time the mixture was cooled to room temperature and concentrated to a dark brown residue under high vacuum. The residue was dissolved in 500 mL of chloroform, washed with two, 50 mL portions of saturated sodium chloride, dried over magnesium sulfate, and concentrated to dryness. Purification of the crude product with liquid chromatography over 200 g of silica gel and eluting with 10% methanol in chloroform provided the analytically pure 3-cyclopentoxy-4-nitrobenzyl alcohol upon drying in vacuo.

Workup

temperaturewas cooled to room temperature
concentrationconcentrated to a dark brown residue under high vacuum
dissolutionThe residue was dissolved in 500 mL of chloroform
washwashed with two, 50 mL portions of saturated sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness
customPurification of the crude product with liquid chromatography over 200 g of silica gel
washeluting with 10% methanol in chloroform

Sources & evidence

ORD record: ord-47a4e39691a1461a9391bd72f42cb0a6
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971959

Linked notes

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