Methanesulfonic Acid → Methyl 3-cyclopropyl-3-(4-hydroxyphenyl)propanoate

HRID 922277Notes

Reaction equation

HRID 922277 reaction equation
[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.[CH3:16]S(O)(=O)=O>CO>[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:5][C:6]([O:8][CH3:16])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 576725253-Cyclopropyl-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 57672485Methyl 3-cyclopropyl-3-(4-hydroxyphenyl)propanoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a 100 mL RB flask fitted with magnetic stirrer and reflux condenser was charged with 5 mL of Methanol. To the stirred solvent was added 3-cyclopropyl-3-(4-hydroxyphenyl)propanoic acid (160 mg, 0.7759 mmol) followed by the addition of Methane sulfonic acid (74.56 mg, 0.7759 mmol). The resulting mixture was stirred at 65° C. for 2 h. After completion of the reaction (reaction monitored by TLC), solvent from the reaction mass was removed under reduced pressure and the resulting crude mass was taken in ethyl acetate (50 mL) and was washed with water (100 mL×3), sodium bicarbonate solution (100 mL×3), saturated brine solution (100 mL). Then the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The product was obtained as brown syrup. yield: 98.0% (0.23 g, crude) (300 MHz, DMSO-d6): δ 9.16 (s, 1H), 7.01-7.04 (d, 2H), 6.64-6.67 (d, 2H), 3.49 (s, 3H), 2.63-2.68 (m, 2H), 2.14-2.22 (m, 1H), 0.93-0.97 (m, 1H), 0.45-0.49 (m, 1H), 0.26-0.33 (m, 1H), 0.13-0.17 (m, 1H), 0.04-0.07 (m, 1H).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. temperaturereflux condenser
  3. customAfter completion of the reaction (reaction monitored by TLC), solvent from the reaction mass
  4. customwas removed under reduced pressure
  5. washwas washed with water (100 mL×3), sodium bicarbonate solution (100 mL×3), saturated brine solution (100 mL)
  6. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customThe product was obtained as brown syrup

Sources & evidence

ORD record
ord-67f0ba12f1d44f66bfb5f7e7939045d6
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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