Water → 10,11-Dihydro-3-methyl-5H-dibenzo[a,d]cyclohepten-5-one

HRID 982348Notes

Reaction equation

HRID 982348 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)([OH:3])=O.O>S1(CCCC1)(=O)=O>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:1](=[O:3])[C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 962WaterHCID 544249322-Carboxy-4'-methyl stilbene

Product 1

HCID 1314562510,11-Dihydro-3-methyl-5H-dibenzo[a,d]cyclohepten-5-oneYield 87.2%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

The acid from Step A (37.5 g) in sulfolane (200 ml) was heated to 110° C. and polyphosphoric acid (150 ml) added. After 1.5 hr at 110° C. the mixture was poured into water (500ml). extracted with hexane (3×200 ml) and the extract washed, dried, diluted with an equal volume of ether and percolated through silica (200 g). The eluate Was evaporated to afford 3-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (30.5 g) as an oil. 60MHz NMR in deuterochloroform 2.35 (CH3), 3.20 ppm [(CH2)2 ].

Workup

  1. extractionextracted with hexane (3×200 ml)
  2. washthe extract washed
  3. customdried
  4. additiondiluted with an equal volume of ether
  5. customThe eluate Was evaporated

Sources & evidence

ORD record
ord-943f8dda2a8b490eb0cb83d30a3a2298
Source dataset
uspto-grants-1991_02
Patent number
US04996211

Reaction notes

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