Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 893390Notes

Reaction equation

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[CH:18]1([O:6][C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=2[O:8][CH3:9])[CH:2]=[O:1])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a magnetically-stirred solution of isovanillin (0.557 mol, 85.0 g) in dry dimethylformamide (500 mL) at room temperature was added powdered K2CO3 (0.558 mol, 77.1 g) in one portion followed by dropwise addition of neat cyclopentyl bromide (0.614 mol, 91.5 g; 65.9 mL). The resulting suspension is warmed to 60° C. and the reaction monitored by TLC until complete. Upon completion, the reaction mixture is cooled to room temperature and the dimethylformamide removed in vacuo. The residue is partitioned between water and ethyl acetate, the aqueous phase extracted with ethyl acetate and the combined organic layers are washed with water. The organics are dried (Na2SO4) and concentrated in vacuo to afford the alkylated product (0.317 mmol, 70.1 g; 57%) as a viscous oil which is of sufficient purity to be used as such in subsequent transformation.

Workup

temperatureUpon completion, the reaction mixture is cooled to room temperature
customthe dimethylformamide removed in vacuo
customThe residue is partitioned between water and ethyl acetate
extractionthe aqueous phase extracted with ethyl acetate
washthe combined organic layers are washed with water
dry with materialThe organics are dried (Na2SO4)
concentrationconcentrated in vacuo
customto afford the alkylated product (0.317 mmol, 70.1 g; 57%) as a viscous oil which

Sources & evidence

ORD record: ord-f36de6b3e32c4a029b610b8a2935329e
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124455

Reaction notes

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