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

HRID 6511
Notes
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Reaction equation

HRID 6511 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 24436Sodium SulfateHCID 148505774-Cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl etherHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 148505794-Formylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 reethanol resulted in 1.4 g of the title compound of melting point 102°-104° C.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with ether
  3. extractionthe organic extract
  4. washwas washed with saturated tartaric acid solution and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customRecrystallization from reethanol

Sources & evidence

ORD record
ord-29b56e7bfb744771ab87ed2781bf6d17
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248823

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes