p-Toluenesulfonic acid → 3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid

HRID 1161098Notes

Reaction equation

HRID 1161098 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([C:15]1[CH:45]=[CH:44][C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]([O:37]C3CCCCO3)[C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31]([OH:33])=[O:32])=[CH:23][CH:22]=2)=[C:17]([Cl:46])[C:16]=1[OH:47])(=[O:14])[CH3:13]>CO.C(OCC)(=O)C>[C:12]([C:15]1[CH:45]=[CH:44][C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH:27]([OH:37])[C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31]([OH:33])=[O:32])=[CH:25][CH:26]=2)=[C:17]([Cl:46])[C:16]=1[OH:47])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 666994513-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid

Product 1

HCID 578844713-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add p-toluenesulfonic acid (16.8 mg, 0.098 mmol) to a solution of 3-[[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid (1.00 g, 1.96 mmol) in methanol (0.20M) and stir overnight. Evaporate solvents, dilute with ethyl acetate and wash with water (1×) and brine (1×). Dry and concentrate to afford the title compound as a white solid (0.786 mg, 1.84 mmol, 94%): MS (m/z): 426 (M−H).

Workup

  1. washwash with water (1×) and brine (1×)
  2. customDry
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-cd00aa0f8a36481382078be72540498e
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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