Water → 3,5-dimethyl-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 982350Notes

Reaction equation

HRID 982350 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1.[CH3:18][Li].O>O1CCCC1.C(OCC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7]([CH3:18])([OH:16])[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 200675883-methyl-5H-dibenzo[a,d]cyclohepten-5-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 200675803,5-dimethyl-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the ketone from Step C (22 g) in dry tetrahydrofuran (400 ml) at 0° C. under nitrogen was added a solution of methyl lithium in diethyl ether (100 ml of 1.4M). The solution was stirred for 1 hr at 0° C. then water was cautiously added and solvents evaporated to give an aqueous mixture which was extracted with ether (2×150 ml). The combined extracts were washed with water, dried and evaporated. Crystallisation from ether/hexane gave 3,5-dimethyl-5H-dibenzo[a,d]cyclohepten-5-ol (20.18 g), m.p. 102°-103° C.

Workup

  1. customsolvents evaporated
  2. customto give an aqueous mixture which
  3. extractionwas extracted with ether (2×150 ml)
  4. washThe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customCrystallisation from ether/hexane

Sources & evidence

ORD record
ord-f7cb29ed22e04703a6a2996a276d4667
Source dataset
uspto-grants-1991_02
Patent number
US04996211

Reaction notes

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