Water → 10,11-dihydro-10,10,11,11tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1605620Notes

Reaction equation

HRID 1605620 reaction equation
[BH4-].[Na+].O.[F:4][C:5]1([F:23])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[C:6]1([F:22])[F:21]>C(O)(C)C>[F:4][C:5]1([F:23])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]([OH:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[C:6]1([F:21])[F:22]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 2037337610,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 2037337210,11-dihydro-10,10,11,11tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 190 mg. (0.0005 mole) of sodium borohydride in 1 ml. of water is added dropwise to a stirred solution of 830 mg. (0.00296 mole) of 10,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-one in 10 ml. of isopropyl alcohol. After stirring the mixture for 3 hours at room temperature and 30 minutes at reflux, the isopropyl alcohol is evaporated under reduced pressure. The residue is partitioned between benzene and water and the benzene extract is separated, washed, and dried. Evaporation under reduced pressure leaves the product as the residual pale yellow oil. A sample for analysis is evaporatively distilled at 80°C. and 0.1 mm.

Workup

  1. temperature30 minutes at reflux
  2. customthe isopropyl alcohol is evaporated under reduced pressure
  3. customThe residue is partitioned between benzene and water
  4. extractionthe benzene extract
  5. customis separated
  6. washwashed
  7. customdried
  8. customEvaporation under reduced pressure
  9. customleaves the product as the residual pale yellow oil
  10. distillationA sample for analysis is evaporatively distilled at 80°C.

Sources & evidence

ORD record
ord-87c3cf96628c4cb19ece530a6ee09947
Source dataset
uspto-grants-1976_04
Patent number
US03950423

Reaction notes

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