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

HRID 1761923ノート

反応式

HRID 1761923 の反応式
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]

参加物

6

反応物 1

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

生成物 1

HCID 345559Methyl 3-formyl-2-hydroxybenzoate収率 85.3%

試薬・触媒・溶媒 4

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9a691dd01d224518852de3522242e240
出典データセット
uspto-grants-1989_05
特許番号
US04829067

反応ノート

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