Hydrochloric Acid → HCID 25111210, compound

HRID 502396Notes

Reaction equation

HRID 502396 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5].Cl[CH:15]([O:17]C)Cl.Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:15]=[O:17])=[CH:10][CH:11]=1)([CH3:5])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 143498Methyl 2-methyl-2-phenylpropanoate

Product 1

HCID 25111210HCID 25111210, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6.80 g (38 mmol) of 2-methyl-2-phenyl-propionic acid methyl ester was dissolved at rt in 200 mL MeCl2 and 7.01 ml (90.4 g=76 mmol) of dichloromethylmethylether was added and the mixture cooled down to 0° C.; 21.47 mL (36.93 g=191 mmol) TiCl4 was added over 15 min and the reaction warmed up to ambient temperature; stirring was continued for 16 hours. The reaction mixture was then treated at 0° C. with 20 ml of HCl (37% in water) and extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by chromatography (silicagel, eluent:gradient of n-heptane/EtOAc) to yield 5.00 g of the title compound as yellow oil. MS: 206.1 (M+).

Workup

  1. temperaturethe reaction warmed up to ambient temperature
  2. extractionextracted twice with MeCl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by chromatography (silicagel, eluent:gradient of n-heptane/EtOAc)

Sources & evidence

ORD record
ord-5cc4fa502e1a4abf8341995c0ee1255f
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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