Sodium Hydroxide → 4-Benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoic Acid

HRID 988243Notes

Reaction equation

HRID 988243 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][C:6]=1[CH3:29])C.[OH-].[Na+]>C(O)C>[CH2:22]([O:21][C:8]1[CH:9]=[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]([C:4]([OH:30])=[O:3])=[C:6]([CH3:29])[CH:7]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18008087Ethyl-4-benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoate

Product 1

HCID 180080944-Benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-4-benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoate (0.57 g, 1.4 mmol) and 10 N sodium hydroxide (1.4 mL, 14 mmol) are combined in ethanol (6 mL) and heated at reflux for 6 hours. The solvent is removed in vacuo and dichloromethane is added to the residue. Then 1 N hydrochloric acid is added to acidify the mixture to pHI. The aqueous layer is extracted once with dichloromethane and the combined organic layers washed once with water. The organic layer is dried over magnesium sulfate and the solvent removed in vacuo to give the title compound as a tan solid. The solid is recrystallized from ethyl acetate/petroleum ether to provide an analytically pure sample; m.p. 109-111° C., 1H NMR (300 MHz, CDCl3) δ 7.18-7.41 (m, 10H), 6.55 (d, 1H), 6.41 (d, 1H), 5.07 (s, 2H), 4.10 (t, 2H), 2.81 (t, 2H), 2.62 (s, 3H), 2.16-2.21 (m, 2H); MS (EI) 376 (M)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customThe solvent is removed in vacuo and dichloromethane
  4. additionis added to the residue
  5. additionThen 1 N hydrochloric acid is added
  6. extractionThe aqueous layer is extracted once with dichloromethane
  7. washthe combined organic layers washed once with water
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7f785a30350b4ed9b4fb28791fe877c8
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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