Ammonium Chloride → HCID 59602259, compound

HRID 1631847Notes

Reaction equation

[CH2:1]1[C:5]2(CCCC3(CCCC3)[C:6]2=[O:15])[CH2:4]CC1.C1C2(CCCCC2=O)CCC1.C[Mg]Cl.[Cl-].[NH4+].[CH3:32][C:33]1([OH:47])[C:42]2([CH2:46][CH2:45][CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][C:34]21[CH2:38][CH2:37][CH2:36][CH2:35]2>O1CCCC1>[C:6]([O:47][C:33]1([CH3:32])[C:34]2([CH2:35][CH2:36][CH2:37][CH2:38]2)[CH2:39][CH2:40][CH2:41][C:42]21[CH2:43][CH2:44][CH2:45][CH2:46]2)(=[O:15])[C:5]([CH3:1])=[CH2:4]

Participants

Conditions

Temperature: 50 °C

Procedure

With stirring under nitrogen atmosphere at 50° C., a mixture of 44.3 g of dispiro[4.1.4.3]tetradecan-6-one (which had been synthesized from spiro[4.5]decan-6-one by a method as described in A. P. Krapcho, Synthesis, 1974, p 383 and references cited therein) and 50 ml of tetrahydrofuran was added dropwise to a tetrahydrofuran solution of 0.43 mol methylmagnesium chloride (which had been prepared from 10.45 g of metallic magnesium, 150 ml of tetrahydrofuran and chloromethane), during which time the temperature was kept below 60° C. The reaction mixture was cooled to room temperature, after which a saturated ammonium chloride aqueous solution was added to stop the reaction. Through ordinary work-up of extraction, washing and drying, and subsequent vacuum distillation, there was obtained 46.3 g (yield 97%) of the target compound, 6-methyldispiro[4.1.4.3]-tetradecan-6-ol.

Workup

customKrapcho, Synthesis, 1974, p 383 and references
customwas kept below 60° C
temperatureThe reaction mixture was cooled to room temperature
customthe reaction
extractionThrough ordinary work-up of extraction
washwashing
customdrying
distillationsubsequent vacuum distillation

Sources & evidence

ORD record: ord-a97e695fb9314a8a8276e16f90bb5fbd
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791288B2

Reaction notes

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