Methanol → (2-Fluoro-4-phenoxyphenyl)-methanol

HRID 911460Notes

Reaction equation

HRID 911460 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:3]=1[CH2:4][O:5]C1CCCCO1.CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOC(C)=O>[F:1][C:2]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 576563912-(2-Fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyran

Product 1

HCID 57656488(2-Fluoro-4-phenoxyphenyl)-methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mix under nitrogen atmosphere 2-(2-fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyran (2.05 g, 6.8 mmol), methanol (60 mL) and p-toluenesulfonic acid monohydrate (260 mg, 1.35 mmol). Stir at ambient temperature for 16 h. Dilute with EtOAc. Wash with saturated aqueous NaHCO3. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo to give the desired intermediate (1.41 g, 95%). MS (ES+) m/z: 201 (M−OH)+.

Workup

  1. washWash with saturated aqueous NaHCO3
  2. customSeparate the organic layer
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-71775c70acfe49d1a588168e31ccb9a5
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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