Lithium hydroxide, monohydrate → 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid

HRID 548720Notes

Reaction equation

HRID 548720 reaction equation
O.[OH-].[Li+].[C:4]1([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)[CH:21]=2)[C:15]([O:17]C)=[O:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C1COCC1>[C:4]1([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)[CH:21]=2)[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127128Methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

Product 1

HCID 576631583-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acidYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (3.78 g; 90.0 mmol) in water (50 mL) was added to a solution of methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (10.0 g, 30 mmol) in THF (100 mL) and the mixture stirred at RT for 18 hours. The THF was removed in vacuo, the aqueous residue treated with 1M hydrochloric acid (90.0 mL) then extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the desired material (9.00 g). 1H NMR δ (CDCl3): 2.0-2.2 (m, 2H), 3.7-3.95 (m, 4H), 4.85 (m, 1H), 5.0 (s, 2H), 6.65 (m, 1H), 7.15 (m, 1H), 7.25-7.4 (m, 6H); m/z 315 (M+H)+.

Workup

  1. customThe THF was removed in vacuo
  2. additionthe aqueous residue treated with 1M hydrochloric acid (90.0 mL)
  3. extractionthen extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fad01814a9c481aa103cad18c118805
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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