Hydrochloric Acid → HCID 18651688, compound

HRID 248192Notes

Reaction equation

HRID 248192 reaction equation
[OH-].[K+].[C:3]([C:7]1[CH:8]=[C:9]([O:17][C@H:18]([CH3:23])[C:19]([O:21]C)=[O:20])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].Cl>O.O1CCCC1>[C:3]([C:7]1[CH:8]=[C:9]([O:17][C@H:18]([CH3:23])[C:19]([OH:21])=[O:20])[CH:10]=[C:11]([C:13]([CH3:14])([CH3:15])[CH3:16])[CH:12]=1)([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54510550HCID 54510550, compound

Product 1

HCID 18651688HCID 18651688, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g (36 mmol) of potassium hydroxide in water (100 mL) and tetrahydrofuran (100 mL) was added 11.48 g (36 mmol) of methyl (2R)-2-(3,5-di-t-butylphenyloxy)propanate (13). The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and the resulting solution was extracted with diethyl ether (3×200 mL). The combined extracts were washed with an aqueous saturated sodium chloride solution (1×300 mL) and dried (MgSO4). Filtration and concentration resulted in a yellowish sludge. The crude product was purified by precipitation from hexane at -78° C. to afford 8.2 g (75%) of (2R)-2-(3,5-di-t-butylphenyloxy)propanoic acid (14) as an off-white crystalline material: 1H NMR (CDCl3) δ1.29 (s, 18 H), 1.64-1.66 (d, 3 H), 4.56-4.82 (q, 1 H), 6.75 (s, 2 H), 7.06 (s, 1 H); 13C NMR (CDCl3) δ177.7, 156.8, 152.5, 116.2, 109.7, 72.3, 35.0, 31.4, 18.4.

Workup

  1. extractionthe resulting solution was extracted with diethyl ether (3×200 mL)
  2. washThe combined extracts were washed with an aqueous saturated sodium chloride solution (1×300 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration
  5. customresulted in a yellowish sludge
  6. customThe crude product was purified by precipitation from hexane at -78° C.

Sources & evidence

ORD record
ord-b2f490f1c76e4805ae2a196505f2e0c1
Source dataset
uspto-grants-1993_05
Patent number
US05208345

Reaction notes

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