Sulfuric Acid → HCID 13676786, compound

HRID 1580813Notes

Reaction equation

HRID 1580813 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14](N)=[O:15])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.S(=O)(=O)(O)[OH:22]>O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]([OH:22])=[O:15])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20459610HCID 20459610, compound

Product 1

HCID 13676786HCID 13676786, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (5-oxo- 10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)acetamide (17.4 g.) in a mixture of concentrated sulphuric acid (d = 1.83; 70 cc.) and water (70 cc.) is heated with vigorous stirring for 3 hours at 100°C. After cooling, the product which precipitates is filtered off and then added to 2N sodium hydroxide solution (200 cc.). The alkaline solution is extracted with diethyl ether and then acidified by adding 2N sulphuric acid (250 cc.). The product which precipitates is filtered off, dried and then recrystallised from ethyl acetate (100 cc.) to give (5-oxo-10,11 -dihydrodibenzo[a,d]cyclohepten-2-yl)acetic acid (11.5 g.) melting at 154°C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. customthe product which precipitates
  4. filtrationis filtered off
  5. additionadded to 2N sodium hydroxide solution (200 cc.)
  6. extractionThe alkaline solution is extracted with diethyl ether
  7. additionby adding 2N sulphuric acid (250 cc.)
  8. customThe product which precipitates
  9. filtrationis filtered off
  10. customdried
  11. customrecrystallised from ethyl acetate (100 cc.)

Sources & evidence

ORD record
ord-ad9f2cf2d7ef4e819758f1c43aa209f3
Source dataset
uspto-grants-1976_01
Patent number
US03933905

Reaction notes

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