Cornforth reagent → 4-Butyryl-2-hydroxy-benzoic acid methyl ester

HRID 1160794Notes

Reaction equation

HRID 1160794 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 595180182-Hydroxy-4-(1-hydroxy-butyl)-benzoic acid methyl ester

Product 1

HCID 595180214-Butyryl-2-hydroxy-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-hydroxy-4-(1-hydroxy-butyl)-benzoic acid methyl ester (132 mg, 0.59 mmol) in DCM (6 mL), is added PDC (245 mg, 1.1 mmol) in one portion. The reaction is stirred overnight. The reaction mixture is filtered through a silica gel plug using DCM as eluent. The filtrate is concentrated to give 4-butyryl-2-hydroxy-benzoic acid methyl ester as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.77 (s, 1H), 7.92 (d, 1H, J=8.4 Hz), 7.52 (d, 1H, J=1.6 Hz), 7.44 (dd, 1H, J=1.6, 8 Hz), 3.99 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 1.76 (qt, 2H, J=7.6 Hz), 1.00 (t, 3H, J=7.6 Hz).

Workup

  1. filtrationThe reaction mixture is filtered through a silica gel plug
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-3f9688a133d74c52aca61d19467a0a7d
Source dataset
uspto-grants-2010_10
Patent number
US07816542B2

Reaction notes

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