4-Hydroxybenzaldehyde → Acetic acid, 2-(4-formylphenoxy)-

HRID 65001

反応式

HRID 65001 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.I[CH2:11][C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].P(=O)(O)(O)O>C(OCC)(=O)C.O>[C:12]([CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([OH:14])=[O:13]

参加物

7

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 1004Phosphoric AcidHCID 5240Iodoacetic AcidHCID 11430Potassium Carbonate

生成物 1

HCID 89177Acetic acid, 2-(4-formylphenoxy)-

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of p-hydroxybenzaldehyde (49 g, 0.40 mol) were added iodoacetic acid (75 g, 0.40 mol) and potassium carbonate (anhydrous, 120 g), and the magnetically stirred mixture was warmed at 60° C. for three days. The resulting solid was dispersed mechanically in a mixture of ethyl acetate (400 ml) and water. The mixture was neutralized cautiously with phosphoric acid. After the dissolution of the solid mass, the neutral aqueous layer was withdrawn. The organic layer was extracted repeatedly with a concentrated solution of dibasic sodium phosphate, to remove additional acidic organic material. The aqueous extracts were combined, filtered through glass wool, and acidified to pH 1 using 6N HCl. This solution was placed in the refrigerator overnight, and a product of tan crystals (21.85 g) was collected. Unreacted p-hydroxybenzaldehyde was recovered upon evaporation of the organic layer. Yield based on recovery of starting material was 60%. Mp 191°-193° C. Analysis (C9H8O4): calc. 60.00% C, 4.48% H; found 59.66% C, 4.37% H.

後処理

  1. dissolutionAfter the dissolution of the solid mass
  2. customthe neutral aqueous layer was withdrawn
  3. extractionThe organic layer was extracted repeatedly with a concentrated solution of dibasic sodium phosphate
  4. customto remove additional acidic organic material
  5. filtrationfiltered through glass wool
  6. customwas placed in the refrigerator overnight
  7. customa product of tan crystals (21.85 g) was collected
  8. customwas recovered upon evaporation of the organic layer
  9. customYield

出典と根拠

ORDレコード
ord-eb0ca224687a45b9ac9c848f9b2d4036
出典データセット
uspto-grants-1986_09
特許番号
US04612315

関連ノート

読み込み中…