Sodium Chloride → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 2246639Notes

Reaction equation

HRID 2246639 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.C(C(CC)=O)C.[Na+].[Cl-]>O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 7288Ethyl ketoneHCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 598551363-(4-Hydroxyphenyl)hex-4-ynoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round-bottom flask was charged with compound M1.2 (37 g), diethyl ketone (160 mL), and water (80 mL). The suspension was heated at reflux for 48 hours. After cooling, the aqueous layer was saturated with NaCl(s) and separated. The organic layer was dried over MgSO4, filtered, and concentrated to a light brown oil, which was crystallized from hot EtOAc:hexanes (1:2). After collecting and drying, the product was obtained as an off-white powder. MS ESI (pos.) m/e: 205.1 (M+H); 227.1 (M+Na). 1H NMR (500 MHz) (DMSO-d6) δ 12.2 (s, 1H); 9.27 (s, 1H); 7.12 (d, 2H, J=8.5 Hz); 6.67 (d, 2H, J=8.6 Hz); 3.87 (m, 1H); 2.54 (m, 2H); 1.82 (d, 3H, J=2.4 Hz).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customseparated
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a light brown oil, which
  8. customwas crystallized from hot EtOAc:hexanes (1:2)
  9. customAfter collecting
  10. customdrying
  11. customthe product was obtained as an off-white powder

Sources & evidence

ORD record
ord-55af50b4b1594947a8c5db1284699713
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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