Oxalyl chloride → 6-(Benzyloxy)naphthalene-2-carbonyl chloride

HRID 343251Notes

Reaction equation

HRID 343251 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=O)[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:25])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([Cl:25])=[O:21])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 144384186-(Benzyloxy)naphthalene-2-carboxylic acid

Product 1

HCID 144384196-(Benzyloxy)naphthalene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heated for refluxing were 2-benzyloxy-6-naphthoic acid of 27.8 g and oxalyl chloride of 15.2 g in toluene of 200 g for 3 hours, and then excess oxalyl chloride and toluene were distilled off under reduced pressure to obtain 2-benzyloxy-6-naphthoyl chloride. This acid chloride was dissolved in toluene of 120 g, and pyridine of 9.5 g and 2-propanol of 6.6 g were added thereto, followed by stirring the solution at 80° C. for 3 hours. Then, after filtering off deposited pyridine hydrochloride, an organic layer was washed with 1N-hydrochloric acid and further washed with water to neutral. The organic layer was separated, and toluene was distilled off under reduced pressure to obtain a crude product. The product was recrystallized from ethanol, whereby 1'-methylethyl 2-benzyloxy-6-naphthoate of 27.2 g was obtained in the form of colorless crystal.

Workup

  1. temperatureHeated
  2. temperaturefor refluxing
  3. customfor 3 hours
  4. distillationexcess oxalyl chloride and toluene were distilled off under reduced pressure

Sources & evidence

ORD record
ord-0023a744f6ce4fcca3576f857cd0c857
Source dataset
uspto-grants-1999_01
Patent number
US05861108

Reaction notes

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