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

HRID 2042995Notes

Reaction equation

HRID 2042995 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.O[Li].O.Cl>C1COCC1.O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:22][CH:23]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 25149898Ethyl 2-(4-((4-(hydroxymethyl)phenyl)ethynyl)phenoxy)acetate

Product 1

HCID 251501162-(4-((4-(Hydroxymethyl)phenyl)ethynyl)phenoxy)ethanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4-((4-(hydroxymethyl)phenyl)ethynyl)phenoxy)acetate (54.0 mg, 0.174 mmol) was dissolved in THF (1 mL), and LiOH.H2O (10.9 mg, 0.261 mmol) in water (0.5 mL) was added. The mixture was stirred for 1.5 h. and 3% HCl (0.5 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 (48.0 mg, 98%). Rf=0.04 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 4.52 (s, 2H, CH2OH); 4.73 (s, 2H, OCH2); 5.26 (s, 1H, CH2OH); 6.95 (d, 2H, J=8.7 Hz, Ph); 7.35 (d, 2H, J=7.8 Hz, Ph); 7.48 (m, 4H, Ph); 12.99 (s, 1H, COOH). 13C-NMR (DMSO-d6): □ 62.0 (CH2OH); 64.0 (OCH2); 87.7 (CC); 88.3 (CC); 114.3, 114.4, 120.3, 126.1, 130.5, 132.3, 142.6, 157.5 (Ph); 169.4 (COO). EI-MS: m/z calculated for C17H14O4 [M]+ 282; [C15H11O2]+ 223; [C8H8O3]+ 152. found 282, 223, 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-5316f5dcd5fc4dc0a3be2b2bc47bd103
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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