Methanol → 3-(Benzyloxy)-5-[(oxan-4-yl)oxy]benzoic acid

HRID 1990252Notes

Reaction equation

HRID 1990252 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:18]=2)[C:12]([O:14]C)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.O.[OH-].[Li+]>C1COCC1.O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:18]=2)[C:12]([OH:14])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 53629680HCID 53629680, compound

Product 1

HCID 591271793-(Benzyloxy)-5-[(oxan-4-yl)oxy]benzoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(phenylmethyl)oxy]-5-(tetrahydro-2H-pyran-4-yloxy)benzoate (9.00 g, 26.3 mmol) was dissolved in THF (120 mL) and methanol (30 mL) added a solution of lithium hydroxide monohydrate (3.24 g, 78.9 mmol) in water (60 mL). The bi-phasic solution was stirred at RT for 3 hours until complete conversion was indicated by LCMS. The organics were removed in vacuo and water (40 mL) added. The pH of the mixture was adjusted to 7 by the addition of hydrochloric acid and the resulting precipitate filtered and washed with cold water to give the desired compound as a white solid (8.03 g). 1H NMR δ (d6-DMSO): 1.57 (m, 2H), 1.94 (m, 2H), 3.50 (m, 2H), 3.84 (m, 2H), 4.62 (m, 1H), 5.15 (s, 2H), 6.87 (t, 1H), 7.09 (m, 1H), 7.14 (m, 1H), 7.34 (t, 1H), 7.40 (t, 2H), 7.46 (d, 2H), 12.99 (s, 1H); m/z 327 (M+H)+

Workup

  1. customThe organics were removed in vacuo and water (40 mL)
  2. additionadded
  3. additionThe pH of the mixture was adjusted to 7 by the addition of hydrochloric acid
  4. filtrationthe resulting precipitate filtered
  5. washwashed with cold water

Sources & evidence

ORD record
ord-cd9b0b250b244235acfbe67235af0652
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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