Dimethyl Sulfoxide → METHYL 7-HYDROXY-2-NAPHTHOATE

HRID 550212Notes

Reaction equation

HRID 550212 reaction equation
C([C:3]([C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([O:17]S(C(F)(F)F)(=O)=O)=[CH:14]2)=[CH:9][CH:8]=1)([OH:6])CC)C.CCN(CC)CC.CS(C)=O.[C]=O.[CH3:38][OH:39]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CCOCC>[CH3:38][O:39][C:3]([C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][C:13]([OH:17])=[CH:12][CH:11]=2)[CH:16]=1)=[O:6]

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 887MethanolHCID 8471TriethylamineHCID 57871420HCID 57871420, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 10081555METHYL 7-HYDROXY-2-NAPHTHOATE

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3283Diethyl EtherSolvent

Procedure

Treat a mixture containing trifluoromethanesulfonic acid 7-(1-ethyl-1-hydroxypropyl)naphthalen-2-yl ester (0.41 g, 14.1 mmol), Pd(OAc)2 (0.30 g, 1.38 mmol), bis-(diphenylphosphino)ferrocene (0.705 g, 1.27 mmol), Et3N (10.2 mL, 73.2 mmol), in MeOH (12 mL) and DMSO (18 mL) with carbon monoxide at 100 psi at 80° C. for 4 h. Pour the reaction mixture into ether (300 mL) and wash with brine (5×100 mL). Add EtOAc (250 mL), wash the organic layer with brine, dry over Na2SO4, and filter. Concentrate the filtrate to give the title compound as a tan solid (2.84 g, quant). 1H NMR (400 MHz, CDCl3) δ 3.98 (s, 3H), 7.23-7.29 (m, 2H), 7.78 (t, J=8.3 Hz, 2H), 7.88-7.90 (m, 1H), 8.43 (d, J=0.88 Hz, 1H).

Workup

  1. additionTreat a mixture
  2. washwash with brine (5×100 mL)
  3. washAdd EtOAc (250 mL), wash the organic layer with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-34ac3c3f97a64cc8a578e8cd36de4948
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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