Sodium Hydroxide → 3-(Benzyloxy)-5-{[(2S)-butan-2-yl]oxy}benzoic acid

HRID 1175881Notes

Reaction equation

HRID 1175881 reaction equation
[CH3:1][C@H:2]([O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=1)[C:9]([O:11]C)=[O:10])[CH2:3][CH3:4].[OH-].[Na+]>C1COCC1>[CH3:1][C@H:2]([O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=1)[C:9]([OH:11])=[O:10])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59127096Methyl 3-{[(1S)-1-methylpropyl]oxy}-5-[(phenylmethyl)oxy]benzoate

Product 1

HCID 591271863-(Benzyloxy)-5-{[(2S)-butan-2-yl]oxy}benzoic acidYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-{[(1S)-1-methylpropyl]oxy}-5-[(phenylmethyl)oxy]benzoate (14.87 g, 47.36 mmol) was vigorously stirred in a mixture of aqueous 1M sodium hydroxide (120 mL) and THF at approximately 45° C. for 4 hours. The bulk of the THF was removed under reduced pressure and the resultant solution partitioned between water and diethyl ether. The aqueous phase was acidified with 2M hydrochloric acid and then extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated in vacuo gave a white solid (11.5 g). 1H NMR δ (CDCl3): 0.90 (t, 3H), 1.20 (d, 3H), 1.49-1.69 (m, 2H), 4.33-4.46 (m, 1H), 5.12 (s, 2H), 6.75-6.79 (m, 1H), 6.99-7.03 (m, 1H), 7.06-7.11 (m, 1H), 7.26-7.47 (m, 5H)

Workup

  1. customThe bulk of the THF was removed under reduced pressure
  2. customthe resultant solution partitioned between water and diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9abe7a9b1ea94ab39e63fb284a041c1a
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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