Dimethylformamide → 1-(1-Naphthyl)-2-naphthol

HRID 2414467Notes

Reaction equation

HRID 2414467 reaction equation
[OH:1][C:2]1[C:11](C(O)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17](C(O)=O)[C:16]=1O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:3]1([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1171502,2′-Dihydroxy[1,1′-binaphthalene]-3,3′-dicarboxylic acid

Product 1

HCID 27552601-(1-Naphthyl)-2-naphthol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 50 g (60 mmol) of Merrifield resin (polCH2Cl where pol=1-2% crosslinked polystyrene, 200-400 mesh beads), 2,2′-dihydroxy-1,1′-binaphthalene-3,3′-dicarboxylic acid (33.7 g), potassium carbonate (12.4 g) and DMF (dimethlyformamide) (350 ml) was heated at 90° C. with stirring for 8 hrs. The color of the resin changed from white to green-yellow. The mixture was diluted with water, filtered, washed with H2O, DMF, and acetone, and then thoroughly dried in the air to give the desired product. IR (KBr, cm−1): 1712 (vs), 1676 (vs).

Workup

  1. filtrationfiltered
  2. washwashed with H2O, DMF, and acetone
  3. customthoroughly dried in the air

Sources & evidence

ORD record
ord-189b200bdb8b489c99e911f7f66f37c2
Source dataset
uspto-grants-2004_11
Patent number
US06812352B2

Reaction notes

Loading…