Sulfuric Acid → HCID 63896650, compound

HRID 1508463Notes

Reaction equation

HRID 1508463 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=1.[C:25](O)([CH3:28])([CH3:27])[CH3:26]>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 63896650HCID 63896650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a fast stirring suspension of anhydrous magnesium sulfate (4.81 g, 40.0 mmol) in dichloromethane (40 ml) was added sulfuric acid (0.55 ml, 10.32 mmol). The reaction was vigorously stirred for 15 minutes at room temperature and then 3-(4-methoxyphenyl)propionic acid (1.8 g, 9.99 mmol) and tert-butanol (4.78 ml, 50.0 mmol) were added. The reaction was sealed and stirred at room temperature overnight. The reaction was quenched with 75 mL of saturated sodium bicarbonate solution and washed with water (2×50 mL) and brine (1×50 mL). The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica gel (0 to 80% ethyl acetate/hexanes) to afford tert-butyl 3-(4-methoxyphenyl)propanoate. 1H NMR (CDCl3, 500 MHz) δ 7.11 (d, J=8.7 Hz, 2H), 6.82 (d, J=8.7 Hz, 2H), 3.78 (s, 3H), 2.85 (t, J=7.7 Hz, 2H), 2.50 (t, J=7.7 Hz, 2H), 1.42 (s, 9H).

Workup

  1. stirringThe reaction was vigorously stirred for 15 minutes at room temperature
  2. customThe reaction was sealed
  3. stirringstirred at room temperature overnight
  4. customThe reaction was quenched with 75 mL of saturated sodium bicarbonate solution
  5. washwashed with water (2×50 mL) and brine (1×50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on silica gel (0 to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f8478ef3f9574ffba453bb6cb14888ef
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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