Methanol → Methyl 4-Formylbenzoate

HRID 77634Notes

Reaction equation

HRID 77634 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:2].S(Cl)(Cl)=O.[CH3:16]O>>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)([O:9][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 15294Methyl 4-FormylbenzoateYield 98%

Conditions

Temperature
0 °C

Procedure

4-Formylbenzoic acid (1ad, 1.00 g, 6.7 mmol) was dissolved in dry methanol (200 ml) and stirred for 10 min at 0° C. Thionyl chloride (6 ml, 82.3 mmol) was added dropwise and the mixture stirred for 90 min at 0° C. and 3 hr at room temperature. The methanol was evaporated and the resulting residue extracted into dichloromethane, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from hexane to give 1.07 g (98%) of a white solid: mp 60-62° C. [expected mp 61° C.]; 1H NMR: δ 3.87 (s, 3H), 8.01 (d, 2H, J=7.9 Hz), 8.13 (d, 2H, J=7.6 Hz), 10.08 (s, 1H); 13C NMR: δ 52.7, 129.7, 129.9, 134.4, 139.1, 165.6, 192.9.

Workup

  1. stirringthe mixture stirred for 90 min at 0° C. and 3 hr at room temperature
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into dichloromethane
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was recrystallized from hexane

Sources & evidence

ORD record
ord-88b954cdddc141e2af7b1bfbcce65408
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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