Sodium Hydroxide → HCID 58551746, compound

HRID 72929Notes

Reaction equation

HRID 72929 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]([O:18][CH3:19])([CH3:17])[CH3:16])[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][CH2:14][C:15]([O:18][CH3:19])([CH3:16])[CH3:17])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58550770HCID 58550770, compound

Product 1

HCID 58551746HCID 58551746, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-methoxy-4-(2-methoxy-2-methyl-propoxy)benzoate (177 mg, 0.66 mmol), dioxane (1.9 mL) and NaOH (1.8 mL of 1 M, 1.80 mmol) were combined and the reaction mixture was heated at 80° C. for 15 minutes. The reaction mixture was concentrated in vacuo and the crude mixture was dissolved in water. The mixture was washed with EtOAc (3×). The aqueous layer was acidified with 1N HCl then washed with EtOAc (3×). The combined organic layers was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to yield 3-methoxy-4-(2-methoxy-2-methyl-propoxy)benzoic acid (130 mg, 77%). ESI-MS m/z calc. 254.1. Found 255.5 (M+1)+; Retention time: 1.14 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 12.61 (s, 1H), 7.54 (dd, J=8.4, 1.9 Hz, 1H), 7.45 (d, J=1.8 Hz, 1H), 7.07 (d, J=8.5 Hz, 1H), 3.89 (s, 2H), 3.81 (s, 3H), 3.17 (s, 3H), 1.22 (s, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe crude mixture was dissolved in water
  3. washThe mixture was washed with EtOAc (3×)
  4. washthen washed with EtOAc (3×)
  5. dry with materialThe combined organic layers was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a09dcc447fa34d2f8c30643152d58058
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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