Hydrochloric Acid → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 1763709노트

반응식

HRID 1763709 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]([O:16]CC)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2.Cl>[OH-].[K+]>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]([OH:16])=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 53675848ethyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2yl)acetate

생성물 1

HCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

시약·촉매·용매 1

HCID 14797Potassium Hydroxide용매

실험 절차

22 G. of 5-oxo-5H-dibenzo[a,d]cycloheptene-2-carboxylic acid is stirred in 200 ml. of chloroform, 50 ml. of thionyl chloride and 1 ml. of dimethylformamide for 8 hours. The mixture is evaporated to dryness and the residue recrystallized from acetonitrile to yield 2-chloroformyl-5-oxo-5H-dibenzo[a,d]cycloheptene. This is dissolved in 200 ml. of chloroform and added to a 3-fold excess of ethereal diazomethane at 0° C. The mixture is left at 0° C for 12 hrs. then evaporated to dryness. The residue is recrystallized from acetonitrile to yield 2-diazoacetyl-5-oxo-5H-dibenzo[a,d]cycloheptene. The diazoketone is heated to reflux in 250 ml. of ethanol and a saturated triethylamine solution of 2 g. of silver benzoate is added slowly until gas evolution ceases. The solution is cooled, filtered and evaporated to yield ethyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetate. This ester is refluxed in 5% aqueous potassium hydroxide for 12 hrs. The solution is cooled, acidified with dilute hydrochloric acid and extracted with ether. The ether extract is dried and evaporated to yield (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid which can be recrystallized from acetone-hexane.

후처리

  1. temperatureThe solution is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. customis dried
  5. customevaporated

출처 및 근거

ORD 기록
ord-7a08a74f3dd94722b0b251f02ecd6f9e
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04112114

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