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

HRID 2040801노트

반응식

HRID 2040801 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 231592103-Ethyl-4-hydroxy-5-methylbenzaldehydeHCID 23668197Sodium Chlorite2회

생성물 1

HCID 592347773-Ethyl-4-hydroxy-5-methyl-benzoic acid수율 92.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52628229b5dd4c4ca0ffa33a3d4bd4ce
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580824B2

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