2,3-Dihydroxybutanedioic Acid → 4-Formylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

HRID 483713

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]#N)=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2.C(O)(=O)C(C(C(O)=O)O)[OH:37].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[O:37])=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2

Participants

Conditions

Temperature: 25 °C

Procedure

15.5 ml (19.7 mmol) of diisobutylaluminum hydride solution (20% in hexane) were added dropwise under nitrogen to a solution of 3 g (9.4 mmol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether in 40 ml of dry ether at 25° C. The mixture was stirred at 25° C. for 40 min and then 250 ml of saturated tartaric acid solution were added dropwise. Subsequently, a little sodium sulfate solution was added, and the phases were separated. The aqueous phase was extracted with ether, and the organic extract was washed with saturated tartaric acid solution and water, dried over Na2SO4 and concentrated. Recrystallization from methanol resulted in 1.4 g of the title compound of melting point 102°-104° C.

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with ether
extractionthe organic extract
washwas washed with saturated tartaric acid solution and water
dry with materialdried over Na2SO4
concentrationconcentrated
customRecrystallization from methanol

Sources & evidence

ORD record: ord-3a18719b85964a5597bd3a8d2ad76551
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225601

Linked notes

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