3-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one → 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol

HRID 274062Notes

Reaction equation

HRID 274062 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([OH:13])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 3444873-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-oneHCID 4311764Sodium borohydride

Product 1

HCID 223918023-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-olYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (7.0 g) in methanol (70 ml), sodium borohydride (1.29 g) was added portionwise at 21°-30° C. and the whole was stirred for 1 hour. The solution was poured into ice water (210 ml) and the resulting precipitate was collected by filtration, washed with water and dried to give 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (6.81 g).

Workup

  1. additionwas added portionwise at 21°-30° C.
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8725762c71a84aa793e45c0776afc080
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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