Hydrochloric Acid → HCID 10443031, compound

HRID 546100Notes

Reaction equation

HRID 546100 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1C=O.[CH2:13]([Mg]Cl)[CH2:14]C.C([O:20][CH2:21][CH3:22])C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[CH:6][C:7]([CH:21]([OH:20])[CH2:22][CH2:13][CH3:14])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 243003Methyl 2-formylbenzoateHCID 178455855HCID 178455855, compound

Product 1

HCID 10443031HCID 10443031, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Formyl-benzoic acid methyl ester (1.00 g, 6.10 mmol) was dissolved in tetrahydrofuran (15 mL), under argon, and chilled to 0° C. A 2.0 M solution of propyl magnesium chloride in diethyl ether (3.05 mL, 6.1 mmol) was added dropwise and the reaction continued to stir at 0° C. for 45 min. 1.0 M aqueous hydrochloric acid solution (10 mL) was added to the reaction and the solution stirred vigorously for 10 min. The solution was diluted with ethyl acetate (100 mL), washed with 1.0 M aqueous hydrochloric acid solution (20 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate and concentrated in vacuo to a clear oil. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 25% ethyl acetate/hexanes) afforded 4-(1-hydroxy-butyl)-benzoic acid methyl ester (610 mg, 48%) as a clear oil: H1-NMR (400 MHz, CDCl3) δ 0.94 (3H, t, J=7.2 Hz), 1.22-1.52 (2H, m), 1.62-1.84 (2H, m), 2.00 (1H, s), 3.91 (3H, s), 4.74 (1H, t, J=6.8 Hz), 7.40 (2H, d, J=8.4 Hz), 7.99 (2H, d, J=8.0 Hz).

Workup

  1. stirringthe solution stirred vigorously for 10 min
  2. washwashed with 1.0 M aqueous hydrochloric acid solution (20 mL), saturated aqueous brine solution (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a clear oil
  5. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-60d78cb277564d268d4b2a674ca05971
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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