Water → HCID 66750940, compound

HRID 643870Notes

Reaction equation

HRID 643870 reaction equation
[OH:1][C:2]1[C:3]([C:13]([OH:15])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7](O)[CH:6]=2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].[OH2:30]>CN(C=O)C>[CH2:16]([O:30][C:13]([C:3]1[C:2]([O:1][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:27][CH2:24][C:2]3[CH:3]=[CH:4][CH:5]=[CH:10][CH:11]=3)=[CH:8][CH:9]=2)[CH:4]=1)=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 7362993,7-DIHYDROXY-2-NAPHTHOIC ACID

Product 1

HCID 66750940HCID 66750940, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,7-dihydroxynaphthalene-2-carboxylic acid (2.04 g, 10 mmol), benzyl bromide (5.98 g, 35 mmol) and potassium carbonate (6.9 g, 50 mmol) in 20 mL of DMF is stirred at 60° C. for 18 h. The mixture is cooled to room temperature, poured into water and extracted into EtOAc. The organic phase is washed with water (3×) and saturated NaCl (1×). The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residual solid is dissolved in a minimum of DCM and filtered through a pad of silica gel using DCM to elute the product. The solvent is removed under reduced pressure to afford 3,7-bis-benzyloxynaphthalene-2-carboxylic acid benzyl ester as a tan solid: mp=99-102° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted into EtOAc
  3. washThe organic phase is washed with water (3×) and saturated NaCl (1×)
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. dissolutionThe residual solid is dissolved in a minimum of DCM
  7. filtrationfiltered through a pad of silica gel
  8. washto elute the product
  9. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-65692a43990c49078f57789cf8d3efd8
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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