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

HRID 2042993Notes

Reaction equation

HRID 2042993 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.O[Li].O.Cl>C1COCC1.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 25150215Ethyl 2-(4-((4-hydroxyphenyl)ethynyl)phenoxy)acetate

Product 1

HCID 251501152-(4-((4-Hydroxyphenyl)ethynyl)phenoxy)ethanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4-((4-hydroxyphenyl)ethynyl)phenoxy)acetate (39.9 mg, 0.135 mmol) was dissolved in THF (1.5 mL) and LiOH.H2O (17.0 mg, 0.405 mmol) in water (1 mL) was added. The mixture was stirred for 2 h. 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 (35.7 mg, 97%) Rf=0.01 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6):□ 4.71 (s, 2H, OCH2); 6.78 (d, 2H, J=8.7 Hz, Ph); 6.93 (d, 2H, J=8.7 Hz, Ph); 7.33 (d, 2H, J=8.1 Hz, Ph); 7.43 (d, 2H, J=8.4 Hz, Ph); 9.87 (s, 1H, OH); 13.00 (s, 1H, COOH). 13C-NMR (DMSO-d6):□ 64.5 (OCH2); 87.2 (CC); 88.6 (CC); 112.8, 114.8, 115.4, 115.7, 132.5, 132.8, 157.6, 157.8 (Ph); 170.0 (COO). MALDI-MS: m/z calculated for C16H12O3 [M]+ 268.0730. found 268.0739.

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-60dc25adab0d4b9ca2e13925087021fd
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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