Hydrochloric Acid → HCID 11817752, compound

HRID 1623629Notes

Reaction equation

HRID 1623629 reaction equation
O[Li].O.[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:10]([CH:21]=1)[C:11]([O:13]CC1C=CC=CC=1)=[O:12].C1COCC1.Cl>C(OCC)(=O)C.O>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:10]([CH:21]=1)[C:11]([OH:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21544507HCID 21544507, compound

Product 1

HCID 11817752HCID 11817752, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiOH.H2O (181 mg, 4.31 mmol) was added to a stirred solution of phenylmethyl 5-(methyloxy)-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 6; 500 mg, 1.44 mmol) in a 3:1 mixture of THF:H2O (40 ml). The mixture was refluxed for 12 h and then diluted with ethyl acetate (50 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a yellow solid. 280 mg.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. customThe organic phase was isolated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe1ef2b0b5f84826bef6d1209d3837cb
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…