Water → HCID 178447074, compound

HRID 1658894Notes

Reaction equation

[CH3:1][C:2]([CH3:13])([CH3:12])[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[CH3:1][C:2]([CH3:13])([CH3:12])[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)=[O:9].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

Conditions

Temperature: -20 °C

Procedure

7,7-Dimethyl-6-oxooctanoylchloride (assumed to be 0.1 mole from the above preparation) in methylene chloride (200 ml) and ferrocene (18.6g; 0.1 mole) were stirred at -20°C and aluminium chloride (13.4g; 0.1 mole) was added over 1 hr. After stirring for a further 2 hrs at -20°C, the reaction had almost gone to completion. Water was added and the organic layer separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with saturated sodium bicarbonate and water, and dried (sodium sulphate) to yield a brown oil which crystallised on addition of petroleum ether and was recrystallised from petroleum ether: cyclohexane (750 ml of 1:1) to yield 7,7-dimethyl-6-oxo-octanoylferrocene as an orange-brown solid. mp 90°-2° (65.3%).

Workup

customthe organic layer separated
extractionThe aqueous layer was extracted with methylene chloride
washthe combined organic layers were washed with saturated sodium bicarbonate and water
dry with materialdried (sodium sulphate)
customto yield a brown oil which
customcrystallised on addition of petroleum ether
customwas recrystallised from petroleum ether

Sources & evidence

ORD record: ord-b617958de6da4f7f9c5bdb30bb54d096
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03966783

Reaction notes

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