Water → HCID 15482431, compound

HRID 600126Notes

Reaction equation

HRID 600126 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:10]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([CH2:24][CH2:25][CH3:26])[C:19]([CH2:27][CH2:28][CH3:29])=[C:18]([CH2:30][CH2:31][CH3:32])[C:17]=3[CH2:33][CH2:34][CH3:35])[C:13]([CH2:36][CH2:37][CH3:38])=[C:12]([C:39](OC)=[O:40])[C:11]=1[C:43](OC)=[O:44])[CH2:8][CH3:9].O.S(=O)(=O)(O)O>C(OCC)C>[OH:40][CH2:39][C:12]1[C:11]([CH2:43][OH:44])=[C:10]([CH2:7][CH2:8][CH3:9])[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([CH2:24][CH2:25][CH3:26])[C:19]([CH2:27][CH2:28][CH3:29])=[C:18]([CH2:30][CH2:31][CH3:32])[C:17]=3[CH2:33][CH2:34][CH3:35])[C:13]=1[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 15482430HCID 15482430, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15482431HCID 15482431, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethyl 1,4,5,6,7,8-hexapropylanthracene-2,3-dicarboxylate obtained in REFERENCE EXAMPLE 2 was used. After lithium aluminum hydride was added to the solution of dimethyl 1,4,5,6,7,8-hexapropylanthracene-2,3-dicarboxylate in diethyl ether at 0° C., the mixture was warmed to room temperature and stirred for an hour. At room temperature, water was added to terminate the reaction. Next, the reaction mixture was rendered slightly acidic with 2N sulfuric acid and extracted with ether. After washing with brine, the extract was dried over anhydrous magnesium sulfate. Column chromatography with silica gel as the packing material was performed using hexane. Recrystallization from hexane gave 6.637 g (13.846 mmols) of the title compound as a light yellow solid. The isolation yield was 98%.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionextracted with ether
  4. washAfter washing with brine
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-72eb894a61fa416f8bd7babfbcf31c4b
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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