Hydrochloric Acid → 3-Ethyl-4-hydroxy-5-methyl-benzoic acid

HRID 2040801ノート

反応式

HRID 2040801 の反応式
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].[O-:13]Cl=O.[Na+].Cl>CS(C)=O.O>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:6]([OH:13])=[O:7])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 231592103-Ethyl-4-hydroxy-5-methylbenzaldehydeHCID 23668197Sodium Chlorite2 回

生成物 1

HCID 592347773-Ethyl-4-hydroxy-5-methyl-benzoic acid収率 92.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒3 回

実験手順

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (78.8 g, 0.48 mol) in DMSO (585 mL), a solution of NaH2PO4 dihydrate (17.3 g, 0.144 mol) in water (160 mL) is added over a period of 13 min. The mixture is stirred at rt an a solution of NaClO2 (65.17 g, 0.577 mol) in water (160 mL) is added while the mixture is cooled with an ice-bath. The mixture is stirred for 1 h before a second portion of NaClO2 (43.44 g, 0.480 mol) in water (100 mL) is added while the temperature is kept between 25 and 40° C. with an ice-bath. The yellow suspension is stirred at rt for 24 h before it is acidified with 32% aq. HCl to pH 2-3. The mixture is extracted with TBME (250 mL), the org. extract is washed with water, and the washings are extracted back with TBME. The solvent of the combined org. extracts is evaporated to give crude 3-ethyl-4-hydroxy-5-methyl-benzoic acid (80.3 g) as a yellow solid.

後処理

  1. additionis added while the mixture
  2. temperatureis cooled with an ice-bath
  3. additionis added while the temperature
  4. customis kept between 25 and 40° C. with an ice-bath
  5. extractionThe mixture is extracted with TBME (250 mL)
  6. extractionextract
  7. washis washed with water
  8. extractionthe washings are extracted back with TBME
  9. customextracts is evaporated

出典と根拠

ORDレコード
ord-52628229b5dd4c4ca0ffa33a3d4bd4ce
出典データセット
uspto-grants-2013_11
特許番号
US08580824B2

反応ノート

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