Hydrochloric Acid → 222191-15-3

HRID 2055724Notes

Reaction equation

HRID 2055724 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH3:7])[C:3]([O:5]C)=[O:4].C[Si](C)(C)[O-].[K+].Cl>C1COCC1.CCOC(C)=O>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 69313255HCID 69313255, compound

Product 1

HCID 9881545222191-15-3

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of methyl 2-methyl-2-(3-phenoxy-phenyl)-propionate (712 mg, 2.63 mmol) in THF (8 mL) was added potassium trimethylsilanolate (90% technical grade; 563 mg; 1.5 eq) and the solution heated to 45° C. for 5 hrs. The solution was allowed to cool, diluted with EtOAc (15 mL) and acidified with 2M HCl to ˜pH 3. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and evaporated to dryness to afford the desired acid, 2-methyl-2-(3-phenoxy-phenyl)-propionic acid, as a colorless powder. 1H NMR (500 MHz, CDCl3) δ 7.25-7.35 (3H, m), 7.08-7.16 (3H, m), 7.01 (2H, dd, J=7.7, 0.6 Hz), 6.86 (1H, dd, J=8.1, 2.3 Hz), 1.58 (6H, s).

Workup

  1. temperatureto cool
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-04eb801bf0804f13ba9fbc66503eb46a
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

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