Sodium borohydride → 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol

HRID 274080Notes

Reaction equation

HRID 274080 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[CH2:11][C:5]=2[CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([OH:12])[CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1055957491495-63-5

Product 1

HCID 200947203-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (220 g) in methanol (1300 ml) was added portionwise sodium borohydride (22.0 g) at 6° C.-30° C., and then the reaction mixture was stirred for 40 minutes and evaporated in vacuo. The residue was partitioned between ethyl acetate (1 l) and water (1 l). The organic layer was washed with 1N hydrochloric acid (500 ml), aqueous sodium hydrogen carbonate (500 ml), and brine (200 ml), and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol as a white powder.

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (1 l) and water (1 l)
  3. washThe organic layer was washed with 1N hydrochloric acid (500 ml), aqueous sodium hydrogen carbonate (500 ml), and brine (200 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0361da08f81c4e1da779d4da0c028911
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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