Hexane → HCID 45281170, compound

HRID 1820158Notes

Reaction equation

[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:45])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:44])=[CH:11]/[CH2:12][CH2:13]/[C:14](/[CH3:43])=[CH:15]/[CH2:16][CH2:17]/[C:18](/[CH3:42])=[CH:19]/[CH2:20][CH2:21]/[C:22](/[CH3:41])=[CH:23]/[CH2:24][CH2:25]/[C:26](/[CH3:40])=[CH:27]/[CH2:28][CH2:29]/[C:30](/[CH3:39])=[CH:31]/[CH2:32][CH2:33]/[C:34](/[CH3:38])=[CH:35]/[CH2:36]O.[CH3:47][O:48][CH:49]1[C:54]([O:55][CH3:56])=[C:53]([OH:57])[CH:52]=[CH:51][C:50]1([OH:59])C.[CH3:60]CCCCC>[N+](C)([O-])=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[CH3:56][O:55][C:54]1[C:49]([O:48][CH3:47])=[C:50]([OH:59])[C:51]([CH3:60])=[C:52]([CH2:36]/[CH:35]=[C:34](\[CH3:38])/[CH2:33][CH2:32]/[CH:31]=[C:30](\[CH3:39])/[CH2:29][CH2:28]/[CH:27]=[C:26](\[CH3:40])/[CH2:25][CH2:24]/[CH:23]=[C:22](\[CH3:41])/[CH2:21][CH2:20]/[CH:19]=[C:18](\[CH3:42])/[CH2:17][CH2:16]/[CH:15]=[C:14](\[CH3:43])/[CH2:13][CH2:12]/[CH:11]=[C:10](\[CH3:44])/[CH2:9][CH2:8]/[CH:7]=[C:6](\[CH3:45])/[CH2:5][CH2:4][CH:3]=[C:2]([CH3:46])[CH3:1])[C:53]=1[OH:57]

Participants

Conditions

Temperature: 50 °C

Procedure

In a 50 ml four necked flask equipped with a stirrer, thermometer, gas inlet, and a reflux condenser, under argon atmosphere 0.654 g (96.52%, 1 mmol) of solanesol (nonaprenol, C45) were dissolved in 15 ml of n-hexane. The solution was mixed with 0.983 g (5.0 mmol) of 2,3-dimethoxy-1,4-dihydroxy-toluene (DMDHT) dissolved in 7.6 ml of nitromethane. The catalyst, Sc(OTf)3 (2.5 mg, 0.005 mmol) was then added. The two-phase mixture was heated up to 50° C. (internal temperature) under stirring (400 rpm). After 16 hours reaction time the mixture was cooled down to room temperature (21° C.). The hexane layer was separated and washed two times with 4 ml (total 8 ml) of nitromethane. The hexane phase was evaporated and yielded 0.78 g of crude 2,3-dimethoxy-5-methyl-6-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl)-benzene-1,4-diol (H2-CoQ9), which was purified by column chromatography on 30 g silica (elution with n-hexane/ethyl acetate=99/1, v/v), to give 440 mg of an orange oil consisting of 73.2% H2-CoQ9 and 21% CoQ9 (formed from H2-CoQ9 by partial air oxidation during isolation and HPLC analysis), corresponding to yields of 40.4% H2-CoQ9 and 11.6% CoQ9, sum 52%.

Workup

customAfter 16 hours reaction time the mixture
temperaturewas cooled down to room temperature (21° C.)
customThe hexane layer was separated
washwashed two times with 4 ml (total 8 ml) of nitromethane
customThe hexane phase was evaporated

Sources & evidence

ORD record: ord-d6d0e8f62f674cfe9d7864cae5edb9ad
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601877B2

Reaction notes

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