Sodium Hydroxide → HCID 66750570, compound

HRID 643871Notes

Reaction equation

HRID 643871 reaction equation
C([O:8][C:9]([C:11]1[C:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]2[C:13](=[CH:14][C:15]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:16][CH:17]=2)[CH:12]=1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>CCO>[CH2:22]([O:21][C:20]1[C:11]([C:9]([OH:10])=[O:8])=[CH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:14]=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66750940HCID 66750940, compound

Product 1

HCID 66750570HCID 66750570, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 3,7-bis-benzyloxynaphthalene-2-carboxylic acid benzyl ester (4.0 g, 8.4 mmol) in EtOH (75 mL), is added 10 mL of 1.0N NaOH (1.2 eq.) and the mixture is stirred at 70° C. for 18 h. The solvent is removed under reduced pressure and the residual solid is dissolved in 250 mL of water. The solution is washed with EtOH and the aqueous phase is acidified with 2N HCl. The resulting precipitate is filtered, washed with water and dried to afford 3,7-bis-benzyloxynaphthalene-2-carboxylic acid as a pale-yellow solid: mp=163-165° C.; (M−H)−=383.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residual solid is dissolved in 250 mL of water
  3. washThe solution is washed with EtOH
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6cc403debd334b3fb4c4a30dcb662816
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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