Methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate → Methyl 3-formyl-2-hydroxybenzoate

HRID 1761923Notes

Reaction equation

HRID 1761923 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:13]2[O:17]C[CH2:15][O:14]2)[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7](OC)=[O:8]>CO.O1CCCC1.C(N(CC)CC)C.[C].[Pd]>[CH:7]([C:6]1[C:5]([OH:12])=[C:4]([CH:3]=[CH:2][CH:11]=1)[C:13]([O:14][CH3:15])=[O:17])=[O:8]

Participants

6

Reactant 1

HCID 19840310Methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate

Product 1

HCID 345559Methyl 3-formyl-2-hydroxybenzoateYield 85.3%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

86 g of methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate are dissolved in a mixture of 700 ml of methanol and 50 ml of tetrahydrofuran, and 70 ml of triethylamine and 7 g of 10% palladium-carbon are added to the solution. The mixture is subjected to catalytic hydrogenation under atmospheric pressure. The reaction mixture is filtered and the filtrate is evaporated to remove solvent. 10% hydrochloric acid is added to the residue and the mixture is concentrated. Water is added to the residue and the aqueous mixture is extracted with ethyl acetate. The extract is dried and evaporated to remove solvent. The resultant crystals are collected, washed with cold ethanol and dried to give 51.1 g of methyl 3-formyl-2-hydroxybenzoate as colorless needles.

Workup

  1. additionare added to the solution
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. customto remove solvent
  5. addition10% hydrochloric acid is added to the residue
  6. concentrationthe mixture is concentrated
  7. additionWater is added to the residue
  8. extractionthe aqueous mixture is extracted with ethyl acetate
  9. customThe extract is dried
  10. customevaporated
  11. customto remove solvent
  12. customThe resultant crystals are collected
  13. washwashed with cold ethanol
  14. customdried

Sources & evidence

ORD record
ord-9a691dd01d224518852de3522242e240
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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