Water → HCID 10471010, compound

HRID 1647260Notes

Reaction equation

HRID 1647260 reaction equation
C[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[O:22][CH3:23])[O:5][C:6]2=[O:13].[CH2:24]([SiH](CC)CC)C.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:24][C:10]1[CH:9]=[C:8]([O:11][CH3:12])[C:7]([C:6]([OH:5])=[O:13])=[C:3]([CH2:4][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[O:22][CH3:23])[CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 19926679HCID 19926679, compound

Product 1

HCID 10471010HCID 10471010, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Methyl-7-methoxy-3-(2',5'-dimethoxyphenyl)-1-(3H)-isobenzofuranone (17 g) and triethylsilane (15 g) were dissolved in dichloromethane (200 ml) and stirred at room temperature under nitrogen. Titanium tetrachloride (5N in CCl4, 25 ml) was added by syringe. The reaction mixture was stirred at room temperature for 4 hours. Water (10 ml) was added dropwise and the reaction mixture was concentrated down. The resulting slurry was dissolved (with heating) in 2N NaOH (aq) and filtered through celite. The filtrate was washed with diethyl ether (2×200 ml) and acidified with concentrated HCl (aq). The resulting precipitate was collected by filtration and dried to give 4-methyl-6-methoxy-2-(2',5'-dimethoxybenzyl)benzoic acid, m.p. 172°-174° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. concentrationthe reaction mixture was concentrated down
  3. dissolutionThe resulting slurry was dissolved
  4. temperature(with heating) in 2N NaOH (aq)
  5. filtrationfiltered through celite
  6. washThe filtrate was washed with diethyl ether (2×200 ml)
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-32c4d8f3304a4054bf76fc61b7b2c415
Source dataset
uspto-grants-1995_07
Patent number
US05430067

Reaction notes

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