Sulfolane → 2-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-one

HRID 596530Notes

Reaction equation

HRID 596530 reaction equation
[C:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)([OH:3])=[O:2].S1([CH2:25][CH2:24][CH2:23][CH2:22]1)(=O)=O.C[C:27]1[CH:42]=[CH:41][C:30]2[C:31](=[O:40])[C:32]3[CH:39]=CC=[CH:36][C:33]=3[CH2:34][CH2:35][C:29]=2[CH:28]=1>O>[C:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:22][CH:14]=1)([OH:3])=[O:2].[CH2:23]([C:24]1[CH:25]=[CH:39][C:32]2[C:31](=[O:40])[C:30]3[CH:41]=[CH:42][CH:27]=[CH:28][C:29]=3[CH2:35][CH2:34][C:33]=2[CH:36]=1)[CH3:22]

Participants

6

Reactant 3

HCID 31347SulfolaneHCID 123988162-[2-(3-Methylphenyl)ethyl]benzoic acidHCID 123988172-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Product 2

HCID 221172892-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-oneHCID 706388133-(o-Carboxyphenethyl)ethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

75 Gm. of 3-(o-carboxyphenethyl)toluene is dissolved in 400 ml. sulpholane and heated to 110°-120° C. 200 Ml. of polyphosphoric acid is added and the mixture is stirred at 100° C. for 90 minutes, and then poured onto ice and water. The mixture is extracted with hexane and the solution dried and evaporated to give 64 gm., 89%, of 2-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one as an oil. Use of 3-(o-carboxyphenethyl)ethylbenzene gives a similar yield of 2-ethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one.

Workup

  1. extractionThe mixture is extracted with hexane
  2. customthe solution dried
  3. customevaporated
  4. customto give 64 gm

Sources & evidence

ORD record
ord-3abb8f04c859485bb5026c13332fec81
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

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