Sulfuric Acid → HCID 15125120, compound

HRID 373376Notes

Reaction equation

HRID 373376 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[CH:11]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](OCC)=[O:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[CH:11]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15125100HCID 15125100, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15125120HCID 15125120, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-(2-hydroxy-3,5,6-trimethylphenyl)-7-phenylheptanoate (1.12 g) in tetrahydrofuran (20 ml) was added lithium aluminum hydride (0.17 g) with ice cooling and the mixture was stirred at room temperature for 3 hours. Diluted sulfuric acid was added to the reaction mixture and it was extracted with ethyl acetate. The organic layer was separated, washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by subjecting it to silica gel column chromatography and eluting with ethyl acetate/hexane (1:4) to obtain 7-(2-hydroxy-3,5,6-trimethylphenyl)-7-phenylheptanol (0.81 g) (Compound 5). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed in turn with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified
  7. washeluting with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-ca1cc322a65247409657880524b01fc1
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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