Hydrochloric Acid → HCID 59602257, compound

HRID 1631845Notes

Reaction equation

[CH3:1][Mg]Cl.[C:4]1(=[O:13])[C:8]2([CH2:12]CC[CH2:9]2)CCC1.[C:14]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl.[C:21]1(C)[CH:26]=CC=[CH:23][CH:22]=1>O1CCCC1>[C:4]([O:19][C:14]1([CH3:1])[C:18]2([CH2:23][CH2:22][CH2:21][CH2:26]2)[CH2:17][CH2:16][CH2:15]1)(=[O:13])[C:8]([CH3:9])=[CH2:12]

Participants

Conditions

Temperature: 40 °C

Procedure

With stirring under nitrogen atmosphere at 40° C., 1300 ml of toluene was added dropwise to a tetrahydrofuran solution of 1.6 mol methylmagnesium chloride (which had been prepared from 39 g of metallic magnesium, 1300 ml of tetrahydrofuran and chloromethane) and then a mixture of 111 g of spiro[4.4]nonan-1-one (which had been synthesized from cyclopentanone by a method as described in A. P. Krapcho, Synthesis, 1974, p 383 and references cited therein) and 1300 ml of toluene added. The reaction mixture was stirred for 1.5 hours at 70° C. and returned to room temperature, after which 20% hydrochloric acid was added to stop the reaction. Through ordinary work-up of extraction, washing and drying, and subsequent vacuum distillation, there was obtained 103 g (yield 83%) of the target compound, 1-methylspiro[4.4]nonan-1-01.

Workup

customKrapcho, Synthesis, 1974, p 383 and references
stirringThe reaction mixture was stirred for 1.5 hours at 70° C.
customreturned to room temperature
customthe reaction
extractionThrough ordinary work-up of extraction
washwashing
customdrying
distillationsubsequent vacuum distillation

Sources & evidence

ORD record: ord-8ef4e58b0a7a4ebfba21ad24123d3095
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791288B2

Reaction notes

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