Ethylene Glycol → 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester

HRID 1576181Notes

Reaction equation

HRID 1576181 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:21]=[CH:20][C:9]2[C:10](=[O:19])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:5].C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:35](O)[CH2:36][OH:37]>CCOCC.O.C(#N)C.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:21]=[CH:20][C:9]2[C:10]3([O:37][CH2:36][CH2:35][O:19]3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:5]

Participants

9

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 24819Phosphorus pentachlorideHCID 123988252-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

Product 1

HCID 537927402-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

1.1 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester is stirred in 10 ml. of benzene containing 0.9 gm. of phosphorus pentachloride for one hour. The solution is then added to a stirred, ice cooled mixture of 2.4 ml. of ethylene glycol, 2.5 ml. of triethylamine, and 13 ml. of acetonitrile. The mixture is allowed to attain room temperature, and then water and ether are added. The ethereal layer is washed several times with water, then dried and evaporated to give a quantitative yield of 2-(5,5-ethylenedioxy-5H-dibenzo [a,d]cyclohepten-2-yl)propionic acid methyl ester. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid methyl ester gives a similar yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid methyl ester.

Workup

  1. additionThe solution is then added to a stirred, ice
  2. temperaturecooled
  3. additionmixture of 2.4 ml
  4. customto attain room temperature
  5. washThe ethereal layer is washed several times with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ffb895968dfe4ba99fc2969303d7b407
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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