Hydrochloric Acid → 2-(4-((3-Hydroxyphenyl)ethynyl)phenoxy)ethanoic acid

HRID 2042991Notes

Reaction equation

HRID 2042991 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.O[Li].O.Cl>C1COCC1.O>[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:21][CH:22]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 25149897Ethyl 2-(4-((3-hydroxyphenyl)ethynyl)phenoxy)acetate

Product 1

HCID 251499002-(4-((3-Hydroxyphenyl)ethynyl)phenoxy)ethanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4-((3-hydroxyphenyl)ethynyl)phenoxy)acetate (48.0 mg, 0.162 mmol) was dissolved in THF (1 mL), and LiOH.H2O (20.4 mg, 0.486 mmol) in water (1 mL) was added. The mixture was stirred over night. and 14% HCl (0.2 mL) was added until pH<1. Water (10 mL) was added, and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc phases was washed with brine (10 mL), dried over MgSO4, and concentrated under reduced pressure. The product was white/yellow and solid (39.5 mg, 92%). Rf=0.02 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 4.52 (s, 2H, CH2OH); 7.1 (m, 8H, Ph); 9.71 (s, 1H, OH); 12.94 (s, 1H, COOH). 13C-NMR (DMSO-d6): □ 64.5 (OCH2); 88.2 (CC); 88.7 (CC); 114.7, 114.9, 116.0, 117.6, 122.0, 123.5, 129.8, 132.9, 157.3, 158.0 (Ph); 169.9 (COO). EI-MS: m/z calculated for C16H12O4 [M]+268; [C14H9O2]+209; [C8H8O3]+ 152. found 268, 207, 152.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×10 mL)
  2. washThe combined EtOAc phases was washed with brine (10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48b0fa05430d4a878acb907ca761ebf5
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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