Potassium Hydroxide → Ethyl (3,5-di-t-butyl-4-oxocyclohexa-2,5-dienylidene)acetate

HRID 850334Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C1C=CC=CC=1.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:12]([C:9]1[C:10](=[O:11])[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][C:7](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=1)([CH3:13])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 40 °C

Procedure

In benzene (150 mL) was dissolved Intermediate 10 (6.7 g, 22.9 mmol) and this treated with a solution of potassium hydroxide (13.9 g [85%], 210 mmol) and potasium ferricyanide (K3Fe(CN)6) (15.2 g, 46 mmol) in water (150 mL). The mixture stirred under nitrogen atmosphere at 40° C. for 2 hours. The benzene layer then separated, washed with brine (100 mL) and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a red oil, 6.1 g (92%), which was used as is.

Workup

customThe benzene layer then separated
washwashed with brine (100 mL)
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo
customto give a red oil, 6.1 g (92%), which

Sources & evidence

ORD record: ord-4eae0ab84fa34408a0f311abf2920d41
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017918

Reaction notes

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