Hydrochloric Acid → HCID 67247052, compound

HRID 2357046Notes

Reaction equation

HRID 2357046 reaction equation
O.[C:2]([O:5][C:6]1[CH:7]=[C:8]([O:16][C:17](=[O:19])[CH3:18])[CH:9]=[C:10]([O:12][C:13](=O)[CH3:14])[CH:11]=1)(=[O:4])[CH3:3].[H-].[Na+].C(Cl)[C:23]1[CH:28]=[CH:27]C=[CH:25][CH:24]=1.Cl>CN(C=O)C>[C:17]([O:16][C:8]1[CH:7]=[C:6]([O:5][C:2](=[O:4])[CH3:3])[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)[CH:9]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 76347Phloroglucinol triacetate

Product 1

HCID 67247052HCID 67247052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Water (4.3 ml, 236 mmol) in DMF (20 ml) was added drop wise at room temperature with stirring to a mixture of acetic acid 3,5-diacetoxy-phenyl ester (refer Kawamoto. H. et. al. Synth. Commun. 26, 531, 1996) (35 g, 139 mmol), NaH (5.66 g, 236 mmol) and benzyl chloride (19.16 ml, 166 mmol) in dry DMF (300 ml). The reaction mixture was stirred overnight (˜16 h), poured into chilled dil. aqueous HCl and extracted with CH2Cl2 to obtain the crude title compound which was purified using flash chromatography (silica gel, 20-50% CH2Cl2 in PE 60-80° C.). Yield, 12.5 g (30%), white solid; mp: 129-30° C.; MS (EI): 300 (M+), 258, 216, 91 (100%); analysis: C17H16O5 requires: C, 67.99; H, 5.37 found: C, 67.50; H, 5.40%.

Workup

  1. additionpoured
  2. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-3a513e5f7d16413bbedc11b5b5eb28de
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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