Sodium Hydroxide → HCID 53929886, compound

HRID 274082Notes

Reaction equation

HRID 274082 reaction equation
C([O:4][C@@H:5]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:7]=2[CH2:6]1)(=O)C.[OH-].[Na+]>CO.O>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:8]2[CH2:9][CH2:10][CH2:11][C@@H:5]([OH:4])[CH2:6][C:7]=2[CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53866555HCID 53866555, compound

Product 1

HCID 53929886HCID 53929886, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl acetate (136 g) in methanol (1.36 l) was added dropwise a solution of sodium hydroxide (46.4 g) in water (232 ml) at ambient temperature. The reaction mixture was stirred for 1 hour and evaporated in vacuo. The residue was partitioned between ethyl acetate (1.1 l) and brine (550 ml). The organic layer was washed with 1N hydrochloric acid solution (550 ml), 1N aqueous sodium hydroxide solution (550 ml), and brine (550 ml), dried over magnesium sulfate, and evaporated in vacuo to give (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (108.96 g) as a white powder.

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (1.1 l) and brine (550 ml)
  3. washThe organic layer was washed with 1N hydrochloric acid solution (550 ml), 1N aqueous sodium hydroxide solution (550 ml), and brine (550 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c6f7a1f01b6413a98dd619ea1b16fd8
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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