Hydrochloric Acid → 3-(4-Methoxyphenyl)-2,2-dimethylpropanoic acid

HRID 602050Notes

Reaction equation

HRID 602050 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]([CH3:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:9]([O:11]CC)=[O:10].Cl>O.O1CCCC1>[CH3:7][C:8]([CH3:23])([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 57470585Ethyl 3-(4-methoxyphenyl)-2,2-dimethylpropanoate

Product 1

HCID 226408683-(4-Methoxyphenyl)-2,2-dimethylpropanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (38.0 g, 0.34 mol) was added to a solution of ethyl 2,2-dimethyl-3-(4-methoxyphenyl)propanoate (40.0 g, 0.17 mol) in a mixture of water (4 mL) and tetrahydrofuran (800 mL) at room temperature and stirred for 16 h. The pH of the reaction mixture was adjusted to ˜2 with 2 N HCl (250 mL) and extracted with EtOAc (800 mL). Aqueous layer was saturated with NaCl and extracted again with EtOAc (800 mL). The combined organic layers were washed with brine (350 mL), dried over Na2SO4, and concentrated to afford 34.0 g (96%) of 2,2-dimethyl-3-(4-methoxyphenyl)propanoic acid as a gummy oil; 1H NMR (200 MHz, CDCl3) δ 7.08 (d, J=8.4 Hz, 2H), 6.80 (d, J=8.4 Hz, 2H), 3.78 (s, 3H), 2.83 (s, 2H), 1.19 (s, 6H).

Workup

  1. extractionextracted with EtOAc (800 mL)
  2. extractionextracted again with EtOAc (800 mL)
  3. washThe combined organic layers were washed with brine (350 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bf99f74e5524707b753d1388dd0c917
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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