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

HRID 15020Notes

Reaction equation

HRID 15020 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-bcb9ef392ef449febaf81ef4d7410c34
Source dataset
uspto-grants-2010_06
Patent number
US07732464B2

Reaction notes

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