Sodium Hydroxide → 2-(benzyloxy)-5-chlorobenzoic acid

HRID 1623669Notes

Reaction equation

HRID 1623669 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([O:9]CC1C=CC=CC=1)=[O:8].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13026912Benzyl 2-benzyloxy-5-chlorobenzoate

Product 1

HCID 33011592-(benzyloxy)-5-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenylmethyl 5-chloro-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 43; 4.16 g, 11.8 mmol), in ethanol (40 ml) and 2M NaOH (20 ml) was heated at reflux for two hours. The mixture was cooled, concentrated in vacuo, acidified with 2M HCl and extracted with ethyl acetate (×3). The organics were washed with brine, dried (MgSO4), and concentrated to give a yellow oil. Purified using biotage chromatography (C18 cartridge, CH3CN/H2O) to give the title compound as a white solid. 1.9 g.

Workup

  1. temperatureat reflux for two hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. extractionextracted with ethyl acetate (×3)
  5. washThe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customPurified

Sources & evidence

ORD record
ord-e8ea0ad95a614e00bc1283ff5fa48f96
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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