Benzoate → HCID 22805680, compound

HRID 1764754Notes

Reaction equation

HRID 1764754 reaction equation
C[Si](O[Si](C)(C)C)(C)C.[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:19](Cl)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Li+].N1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[C:10]([O:18][C:10]1[CH:11]=[CH:12][C:21]2[C@H:22]3[CH2:31][CH2:32][C:33]4[C@H:15]([C@@H:23]3[CH2:24][CH2:25][C:20]=2[CH:19]=1)[CH2:14][CH2:13][C:34]=4[CH3:35])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 242BenzoateHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 24764HexamethyldisiloxaneHCID 433294Lithium Chloride

Product 1

HCID 22805680HCID 22805680, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

After an unsuccessful attempt to convert the trimethylsilyl ether directly to the benzoate 7a (R = C6H5CO2) by heating with benzoyl chloride and lithium chloride in pyridine, the trimethylsilyl group was completely hydrolyzed by brief (about 1 minute) reflux in methanol. After removal of the methanol at reduced pressure, the benzoate-phenol mixture was treated with 2 ml of benzoyl chloride in 25 ml of pyridine for 10 minutes, followed by 2 ml of 85% lactic acid for 10 minutes to destroy excess reagent. The mixture was poured into water, extracted with ether, and the ether layer was thoroughly washed with dilute H2SO4 and saturated NaHCO3, followed by the usual work up to afford 4.02 g (theoretical yield 3.84 g) of brown crystalline solide, mp 100°-120°. An analytical sample was obtained by recrystallization from methanol, colorless plates, mp 114°-116°.

Workup

  1. customwas completely hydrolyzed by brief (about 1 minute)
  2. customAfter removal of the methanol at reduced pressure
  3. additionthe benzoate-phenol mixture was treated with 2 ml of benzoyl chloride in 25 ml of pyridine for 10 minutes
  4. customto destroy excess reagent
  5. additionThe mixture was poured into water
  6. extractionextracted with ether
  7. washthe ether layer was thoroughly washed with dilute H2SO4 and saturated NaHCO3
  8. customto afford 4.02 g (theoretical yield 3.84 g) of brown crystalline solide, mp 100°-120°

Sources & evidence

ORD record
ord-aff2d2998fd7499d9fe5a6892fc606ef
Source dataset
uspto-grants-1978_09
Patent number
US04117234

Reaction notes

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