Sodium Hydroxide → HCID 58551178, compound

HRID 1908089Notes

Reaction equation

HRID 1908089 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][C@@H:14]1[CH2:18][CH2:17][O:16][CH2:15]1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][C@@H:14]1[CH2:18][CH2:17][O:16][CH2:15]1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58551520HCID 58551520, compound

Product 1

HCID 58551178HCID 58551178, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To (R)-methyl 3-methoxy-4-(tetrahydrofuran-3-yloxy)benzoate (0.95 g, 3.8 mmol) were added dioxane (10 mL) and NaOH (10 mL, 1M) and the mixture was heated at 80° C. for 0.5 h. The solvent was evaporated under reduced pressure and the residue was dissolved in water and was washed with EtOAc (×3). The aqueous layer was acidified and a solid was formed. The aqueous layer (with the solid) was washed with EtOAc (×3). The combined organics were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to yield (R)-3-methoxy-4-(tetrahydrofuran-3-yloxy)benzoic acid (0.71 g, 79%) as a white solid. ESI-MS m/z calc. 238.1. found 239.3 (M+1)+; Retention time: 1.21 minutes (4 min run). 1H NMR (400 MHz, DMSO) δ 12.70 (s, 1H), 7.54 (dd, J=8.3, 1.4 Hz, 1H), 7.46 (d, J=1.3 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 5.13-5.02 (m, 1H), 4.04-3.62 (m, 7H), 2.40-2.12 (m, 1H), 2.10-1.86 (m, 1H). The following compounds were synthesized using the procedures described above: (R)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methoxybenzoic acid, (S)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methoxybenzoic acid, and 4-(3-hydroxycyclopentyloxy)-3-methoxybenzoic acid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washwas washed with EtOAc (×3)
  4. customa solid was formed
  5. washThe aqueous layer (with the solid) was washed with EtOAc (×3)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-14e5647ccb0e4b16b3d988a4b70495f4
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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