Sodium Hydroxide → 9-methoxy-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid

HRID 1782053Notes

Reaction equation

HRID 1782053 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([O:18]C)=[O:17])=[CH:7][CH:6]=1>C1COCC1>[CH3:3][O:4][C:5]1[C:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57438494HCID 57438494, compound

Product 1

HCID 227338869-methoxy-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A NaOH solution (500 ml, 2N) was added to a solution of intermediate (7) in THF (250 ml). The mixture was stirred at room temperature overnight. The solvent was evaporated partially. The residue was extrated with DCM. The mixture was separated into its layers. The aqueous layer was acidified with a concentrated HCl solution until pH=1 to 2. The solid was filtered off, washed with water and dried, yielding 35.5 g of 9-methoxy-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid (intermediate 8).

Workup

  1. customThe solvent was evaporated partially
  2. customThe mixture was separated into its layers
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d2bdae1019994c7aaf9cdb2c198814c4
Source dataset
uspto-grants-2009_03
Patent number
US07498347B2

Reaction notes

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