Methanol → HCID 18326277, compound

HRID 1250464Notes

Reaction equation

HRID 1250464 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])=[C:6]([Cl:16])[CH:5]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:16][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53777615HCID 53777615, compound

Product 1

HCID 18326277HCID 18326277, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-Chloro-4-(4-nitrilo-butoxy)-benzoic acid methyl ester (6.24 g, 24.6 mmol in THF (100 ml) and methanol (100 ml) was treated with 5 N sodium hydroxide solution (35 ml) with stirring at room temperature for 1 h. The reaction mixture was concentrated in vacuo, diluted with water, and acidified to pH 1 with 5 N hydrochloric acid. The resulting suspension was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The resulting off white solid was triturated with hot petroleum ether, cooled and filtered to give 5.58 g (95%) of the title compound as a white solid mp 150° C.; 1H NMR (CDCl3) δ2.22-2.28 (m, 2H), 2.69 (t, J=7.0 Hz, 2H), 3.90 (s, 3H), 4.23 (t, J=5.5 Hz, 2H), 6.97 (d, J=8.6 Hz, 1H), 8.01 (dd, J=8.6, 2.2 Hz, 1H), 8.14 (d, J=2.0 Hz, 1H). IR (KBr) 3400, 2200, 1700, 1600, 1450, 1275 and 1050 cm−1, mass spectrum (EI), m/z 239/241. Anal. Calcd. for C11H10ClNO3: C, 55.13; H, 4.21; N, 5.85. Found: C, 54.84; H, 4.01; N, 5.69.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionThe resulting suspension was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting off white solid was triturated with hot petroleum ether
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-31db4140861f4379858a1a4f4d71aa36
Source dataset
uspto-grants-2002_01
Patent number
US06339064B1

Reaction notes

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