Benzonitrile, 4-bromo- → 4-(8-Hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)benzonitrile

HRID 1461791Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=O)[O:17][CH2:16]1.C1C[O:29]CC1.CCCCCC>>[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)([OH:29])[CH2:20][CH2:19]2)[O:17][CH2:16]1

Participants

Reactant 4

HCID 12162Benzonitrile, 4-bromo-

HCID 123480741,4-Dioxaspiro[4.5]decan-6-one

HCID 21883165Tetrahydrofuran hexane

HCID 178418339Butyllithium

Product 1

HCID 150239054-(8-Hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)benzonitrileYield 70%

Procedure

4-Bromobenzonitrile was treated in THF-hexane with n-butyllithium at -100° C. Cyclohexanedione monoethylene ketal was added at -100° to give 70% yield of 11.

Sources & evidence

ORD record: ord-83fccd9e25934bc7b89a55d5fce0a6c0
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05077404

Reaction notes

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