Benzyl Bromide → Phenylmethyl 2-hydroxy-1-naphthalenecarboxylate

HRID 1596043Notes

Reaction equation

HRID 1596043 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO.CN(C=O)C.[Cl-].[Na+].O>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 167902-Hydroxy-1-naphthoic acid

Product 1

HCID 12139612Phenylmethyl 2-hydroxy-1-naphthalenecarboxylateYield 57%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-hydroxy-1-carboxynaphthalene (4.70 g, 25.0 mmol) and 20% cesium carbonate (20.3 mL, 12.5 mmol) in methanol (20 mL) was striped to dryness, dissolved in DMF (10 mL), treated with benzyl bromide (2.67 mL, 22.5 mmoL), stirred for 20 hours, diluted with brine, and extracted with ethyl acetate. The ethyl acetate was washed with water, 1 M NaOH, water and brine, dried (MgSO4), filtered, and concentrated to provide 3.98 g (57%) of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with water, 1 M NaOH, water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a86940ab39344b7790e3f2c04a92261d
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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