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

HRID 1993017

Reaction equation

HRID 1993017 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 acidYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L RB flask was charged with compound 1.2 (37 g), diethyl ketone (160 mL), and water (80 mL). The suspension was heated to reflux for 48 h. 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 ethyl acetate:hexanes (1:2). After collecting and drying, the product was obtained as an off-white powder (20.3 g, 77%). 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). MS ESI (pos.) m/e: 205.1 (M+H); 227.1 (M+Na).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 48 h
  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 ethyl acetate:hexanes (1:2)
  9. customAfter collecting
  10. customdrying

Sources & evidence

ORD record
ord-a5b9845883ef4f078b7cd95f0ab6d9a8
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Linked notes

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