Methanol → Methyl 3-formyl-2-hydroxybenzoate

HRID 1357454Notes

Reaction equation

HRID 1357454 reaction equation
S(=O)(=O)(O)O.BrC(CC(O[C:13]1[CH:22]=[CH:21][CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:14]=1[OH:23])=O)Br.[OH2:24].[CH3:25]O>>[CH:25]([C:13]1[C:14]([OH:23])=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:24]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 70018491Methyl 3-(1,1-dibromo)methylacetoxysalicylate

Product 1

HCID 345559Methyl 3-formyl-2-hydroxybenzoate

Conditions

Temperature
22.5 °C

Procedure

63 ml of concentrated sulfuric acid were added dropwise at approximately 20 to 25° C. to a solution of 64 g (0.17 mol) of the dibromide of Example 1 in 500 ml of anhydrous methanol. The temperature of the reaction solution was kept at 30° C. by cooling. After the mixture had been stirred for 30 minutes at 20 to 25° C., it was heated for 3 hours to 50° C. The reaction mixture was stirred into approximately 3.5 l of water. The precipitate was filtered off and washed with water and then with a pentane/MTBE mixture (5:1). After drying, 25 g of the title compound were obtained, which corresponds to 81% of theory. (m.p. 82° C.)

Workup

  1. customwas kept at 30° C.
  2. temperatureby cooling
  3. temperatureit was heated for 3 hours to 50° C
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customAfter drying

Sources & evidence

ORD record
ord-9865bf0f7b7a4d7486f92df751020322
Source dataset
uspto-grants-2003_07
Patent number
US06593315B2

Reaction notes

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