Hydrochloric Acid → HCID 57581231, compound

HRID 548553Notes

Reaction equation

HRID 548553 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:19]=[C:18]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:17]=2)=[CH:8][CH:7]=1.[Li+].[OH-].O.Cl>C1COCC1.CO>[C:24]1([C:23]#[C:22][C:20]2[CH:21]=[C:16]([C:15]#[C:14][CH2:13][O:12][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:38])=[O:2])=[CH:11][CH:10]=3)[CH:17]=[C:18]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:19]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67158074HCID 67158074, compound

Product 1

HCID 57581231HCID 57581231, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {4-[3-(3,5-bis-phenylethynyl-phenyl)-prop-2-ynyloxy]-phenoxy}-acetic acid methyl ester (0.26 g, 0.51 mmol) in THF (5.6 ml) and methanol (1.1 ml) was added a ice-cold solution of LiOH (1 M, 5.6 ml). The reaction mixture was stirred at 0° C. for 45 min., after which water (37 ml) and aqueous HCl (1M, 7.5 ml) were added. The mixture was extracted with ethyl acetate (2×25 ml), and the combined organic phases were dried and evaporated to give the title compound in 240 mg (96%) yield.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×25 ml)
  2. customthe combined organic phases were dried
  3. customevaporated

Sources & evidence

ORD record
ord-aa874f2b2f354986bfddad6000c182fe
Source dataset
uspto-grants-2011_05
Patent number
US07943612B2

Reaction notes

Loading…