Methanol → HCID 21518340, compound

HRID 1580818Notes

Reaction equation

HRID 1580818 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.[CH3:22][OH:23].N1C=CC=CC=1>C(Cl)Cl.C(OCC)C.O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([O:23][CH3:22])=[O:15])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

7

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 21518331HCID 21518331, compound

Product 1

HCID 21518340HCID 21518340, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(5-oxo-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)propionyl chloride (10 g.) in methylene chloride (100 cc.) is added at 20°C. and over the course of 10 minutes to a mixture of methanol (100 cc.) and anhydrous pyridine (10 cc.). On concentrating the reaction mixture to dryness, a paste-like residue (weighing 14 g.) is obtained and the latter is taken up in diethyl ether (500 c.) and water (100 cc.). The ether phase is decanted, washed twice with water (total 100 cc.) and dried over potassium carbonate. On concentrating to dryness, methyl 2-(5-oxo-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)propionate (8.6 g.) is obtained.

Workup

  1. concentrationOn concentrating the reaction mixture to dryness
  2. customa paste-like residue (weighing 14 g.) is obtained
  3. customThe ether phase is decanted
  4. washwashed twice with water (total 100 cc.)
  5. dry with materialdried over potassium carbonate
  6. concentrationOn concentrating to dryness

Sources & evidence

ORD record
ord-ea2ca28cc53543a99ad3b571ed49c976
Source dataset
uspto-grants-1976_01
Patent number
US03933905

Reaction notes

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