Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 2210535Notes

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=O)C>[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 (557 mmol, 85.0 g) in dry DMF (500 mL) at room temperature was added powdered K2CO3 (558 mmol, 77.1 g) in one portion followed by the dropwise addition of neat cyclopentyl bromide (614 mmol, 91.5 g; 65.9 mL). The resulting suspension was warmed to 60° C. and the reaction monitored by TLC until complete. Upon completion, the reaction mixture was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between H2O and EtOAc, the aqueous phase extracted with EtOAc and the combined organic layers were washed with H2O. The organics were dried (Na2SO4) and concentrated in vacuo to afford the alkylated product (317 mmol, 70.1 g; 57%) as a viscous oil which was of sufficient purity to be used as such in subsequent transformation.

Workup

temperatureUpon completion, the reaction mixture was cooled to room temperature
customthe DMF was removed in vacuo
customThe residue was partitioned between H2O and EtOAc
extractionthe aqueous phase extracted with EtOAc
washthe combined organic layers were washed with H2O
dry with materialThe organics were dried (Na2SO4)
concentrationconcentrated in vacuo
customto afford the alkylated product (317 mmol, 70.1 g; 57%) as a viscous oil which

Sources & evidence

ORD record: ord-2b301a8ac81f4312b8e519eac1b20d1e
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05459151

Reaction notes

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