Sulfuric Acid → HCID 15482393, compound

HRID 600135Notes

Reaction equation

HRID 600135 reaction equation
[CH2:1]([C:4]1[C:13]([CH2:14][CH2:15][CH3:16])=[C:12]([CH2:17][CH2:18][CH3:19])[C:11]([CH2:20][CH2:21][CH3:22])=[C:6]([C:7](OC)=[O:8])[C:5]=1[C:23](OC)=[O:24])[CH2:2][CH3:3].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>O>[OH:8][CH2:7][C:6]1[C:11]([CH2:20][CH2:21][CH3:22])=[C:12]([CH2:17][CH2:18][CH3:19])[C:13]([CH2:14][CH2:15][CH3:16])=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]=1[CH2:23][OH:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 15482391Dimethyl 3,4,5,6-tetrapropylbenzene-1,2-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15482393HCID 15482393, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 3,4,5,6-tetrapropylphthalate (5.22 g, 14.4 mmols) was added at 0° C. to a 50 ml THF solution of LiAlH4 (1.20 g, 31.7 mmols). After stirring at room temperature for an hour, water was added for hydrolysis. The mixture was treated with 2N H2SO4 followed by extraction with diethyl ether. Subsequently, the extract was washed with brine and dried over anhydrous magnesium sulfate. Column chromatography was performed using silica gel as the packing material to give the title compound (3.67 g) as a white solid. The isolation yield was 91%.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washSubsequently, the extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-b97a5789da9c4d6ab64f1024faf57cdc
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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