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

HRID 1761923노트

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HRID 1761923 반응식
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]

참가 물질

6

반응물 1

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

생성물 1

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

시약·촉매·용매 4

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a691dd01d224518852de3522242e240
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04829067

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