Benzoyl chloride → 1,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester

HRID 442657Notes

Reaction equation

HRID 442657 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.Cl[Sn](Cl)(Cl)Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O>[C:20]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 4069581,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of methyl 3,4-methylenedioxyphenylacetate (150 mg, 0.77 mmol) in CH2Cl2 (5 mL) was added SnCl4 (1.0M solution in CH2Cl2 ; 1.5 mL, 1.5 mmol) at 0° C. Then benzoyl chloride (130 μL, 1.1 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature. After 24 h, the mixture was added to a saturated NaHCO3 solution (30 mL), diluted with 1:1 hexane/EtOAc (60 mL), washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc) to yield the title compound (110 mg, 48%). 1H NMR (CDCl3) 7.78-7.45 (m, 5H), 6.88 (s, 1H), 6.84 (s, 1H), 6.04 (s, 2H), 3.80 (s, 2H), 3.61 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-e441c82b165346df89d10a8470b72bed
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

Loading…