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

HRID 1599116

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. Tie aqueous phase was extracted with ether, and the organic extract was washed with saturated tartaric acid solution and water, dried over Na2SO, 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
extractionwas extracted with ether
extractionthe organic extract
washwas washed with saturated tartaric acid solution and water
dry with materialdried over Na2SO
concentrationconcentrated
customRecrystallization from methanol

Sources & evidence

ORD record: ord-d55111c78d6044bda1368f0c7cb0a19d
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739374

Linked notes

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