Potassium Hydroxide → 4-Ethynyl-3-(3-methoxypropoxy)benzoic acid

HRID 1158395Notes

Reaction equation

HRID 1158395 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[C:6]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=1.[OH-].[K+]>CO>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][C:6]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])#[CH:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68445353Methyl 3-(3-methoxypropoxy)-4-[(trimethylsilyl)ethynyl]benzoate

Product 1

HCID 862481424-Ethynyl-3-(3-methoxypropoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(3-methoxy-propoxy)-4-trimethylsilanylethynyl-benzoic acid methyl ester (16.49 mmol) in MeOH (40 mL) is added KOH (1 N, 24.7 mL, 24.7 mmol). The resulting mixture is stirred at RT for 15 h and concentrated under reduced pressure. The residue was taken up in HCl (2 N, 100 mL) and extracted with AcOEt (100 mL×3). The combined organic extracts are washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title as a yellow oil which is used without further purification in the next step. MS (FAB): 235.0 [M+H]+. 1H-NMR (CDCl3, 300 MHz): δ=2.15 (p, 2H), 3.38 (s, 3H), 3.41 (s, 1H), 3.62 (t, 2H), 4.22 (t, 2H), 7.5 (d, 1H), 7.65 (s, 1H), 7.68 (d, 1H) ppm.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with AcOEt (100 mL×3)
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the title as a yellow oil which
  7. customis used without further purification in the next step

Sources & evidence

ORD record
ord-1619bed8986048b09bfdd284f2bcad1e
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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