Hydrochloric Acid → HCID 18182605, compound

HRID 1264216Notes

Reaction equation

HRID 1264216 reaction equation
C[O:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+].Cl>CO.C1COCC1.CCOCC>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:18])=[O:2])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21350305HCID 21350305, compound

Product 1

HCID 18182605HCID 18182605, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionic acid methyl ester (2.0 g, 8.2 mmol) (reference example 30a) in MeOH/THF (20 mL, 1/1) is added NaOH (2 mL, 6M). The resulting solution is stirred for 1 hour then heated to 65° C. and stirred at this temperature for 2 hours. The reaction mixture is then cooled and acidified (to pH 1) with hydrochloric acid (2 M). The resulting mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated to give 1.78 g of the title compound as a solid. 1H NMR (CDCl3) d 1.61 (s, 6H), 6.45 (dd, J 3, 2 Hz, 1H), 6.62 (d, J=3 Hz, 1H), 7.42 (m, 2H), 7.45 (d, J=2 Hz, 1H), 7.64 (m, 2H). MS (EI) m/z 230 (M+)

Workup

  1. stirringstirred at this temperature for 2 hours
  2. temperatureThe reaction mixture is then cooled
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5dc483d59ff42a4b9e6ce97da87d3e7
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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