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

HRID 2041340Notes

Reaction equation

HRID 2041340 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 16h. 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-079a7785ffe544e087f4fd046ee169fa
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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