Methanol → Methyl 2,6-dimethylbenzoate

HRID 64563

反応式

HRID 64563 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>S(Cl)(Cl)=O.N1C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5]

参加物

5

反応物 2

HCID 887MethanolHCID 124392,6-Dimethylbenzoic acid

生成物 1

HCID 519028Methyl 2,6-dimethylbenzoate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 10 g of 2,6-dimethylbenzoic acid in 22 g thionyl chloride was stirred at reflux temperature for 2 hours. Removal of the excess thionyl chloride afforded the crude acid chloride as a yellow oil. This intermediate was added to a stirred solution of 4 mL of methanol in 10.8 mL pyridine at 65°-70° C. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours and then poured into 75 mL ice-water. The aqueous layer was extracted with four 50-mL portions of ether and the combined organic extracts were backwashed with saturated sodium bicarbonate solution, 5% aqueous hydrochloric acid, and water. Drying and evaporation of the solvent gave a pale yellow oil which was purified by bulb-to-bulb distillation (40°-50° C., 0.5 mm Hg) to afford 9.5 g of pure 2,6-dimethylbenzoic acid, methyl ester as a colorless liquid; IR (film) 1725 cm-1 ; NMR(CDCl3) δ 2.3 (s, 6H), 3.9 (s, 3H), 7.0-7.4 (m, 3H).

後処理

  1. temperatureat reflux temperature for 2 hours
  2. customRemoval of the excess thionyl chloride
  3. customafforded the crude acid chloride as a yellow oil
  4. additionAfter completion of the addition
  5. extractionThe aqueous layer was extracted with four 50-mL portions of ether
  6. customDrying
  7. customevaporation of the solvent
  8. customgave a pale yellow oil which
  9. distillationwas purified by bulb-to-bulb distillation (40°-50° C., 0.5 mm Hg)

出典と根拠

ORDレコード
ord-db5b6ed508d24926b574319c1fe5966e
出典データセット
uspto-grants-1986_09
特許番号
US04609395

関連ノート

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