Sulfuric Acid → HCID 15482428, compound

HRID 600140Notes

Reaction equation

HRID 600140 reaction equation
[CH2:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][CH2:15][CH3:16])=[C:6]([C:17](OC)=[O:18])[C:5]=1[C:21](OC)=[O:22])[CH2:2][CH3:3].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>O>[OH:18][CH2:17][C:6]1[C:5]([CH2:21][OH:22])=[C:4]([CH2:1][CH2:2][CH3:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 11290387HCID 11290387, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15482428HCID 15482428, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 1,4-dipropylnaphthalene-2,3-dicarboxylate (0.295 g, 0.898 mmol) was added to a 5 ml THF solution of LiAlH4 (0.075 g, 1.98 mmol) at 0° C. After stirring at room temperature for an hour, water was added to effect hydrolysis. The mixture was treated with 2N H2SO4 followed by extraction with diethyl ether. The extract was washed with brine and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure. The title compound (0.219 g) was obtained as a white solid. The isolation yield was 90%.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1bba02aafe1a46f68326d60983ad5d77
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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