Toluene → HCID 54031428, compound

HRID 1598628Notes

Reaction equation

HRID 1598628 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[CH:14]=[C:13]([CH:15](O)[CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][C:10]=1[O:26][CH3:27]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:8][C:9]1[CH:14]=[C:13]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH:12]=[CH:11][C:10]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 1140TolueneHCID 54295172HCID 54295172, compound

Product 1

HCID 54031428HCID 54031428, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 1M solution of titanium tetrachloride in toluene (74.1 mL, 74.1 mmol) was added dropwise to a solution of 2-methyl-4-(1-hydroxy-4-phenyl-1-butyl) anisole (5.0 g, 18.5 mmol) in methylene chloride. The mixture was stirred at room temperature for 3h, then the reaction was quenched by pouring into excess aqueous saturated sodium bicarbonate. After stirring for 5 min the mixture was extracted with ether, and the organic phase was dried over magnesium sulfate, concentrated, and purified by chromatography over silica gel eluted with hexanes to afford 2.46 g of 2-methyl-4-(1-tetralinyl) anisole as a clear oil.

Workup

  1. customthe reaction was quenched
  2. additionby pouring into excess aqueous saturated sodium bicarbonate
  3. extractionwas extracted with ether
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by chromatography over silica gel
  7. washeluted with hexanes

Sources & evidence

ORD record
ord-fe25f38082364e6d89d95b08faa07b3e
Source dataset
uspto-grants-1998_04
Patent number
US05739140

Reaction notes

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