Hydrochloric Acid → 7-(Benzyloxy)-2-naphthoic acid

HRID 890955Notes

Reaction equation

HRID 890955 reaction equation
[OH-:1].[K+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([C:21]#N)=[CH:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC=CC=1.Cl.[OH2:31]>C(O)C>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([C:21]([OH:31])=[O:1])=[CH:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 222434287-(Benzyloxy)naphthalene-2-carbonitrile

Product 1

HCID 222434307-(Benzyloxy)-2-naphthoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

KOH (406 mg, 7.3 mmol) is added to a suspension of 7-benzyloxy-2-naphthonitrile (626 mg; 2.42 mmol) in water, ethanol, and toluene (15 mL, 1:3:2). The reaction is heated to 80° C. for 72 hours. The reaction is allowed to cool, poured into 1M HCl and extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The product is purified by column chromatography (step gradient, 5 to 10% methanol in CH2Cl2). The resulting material is crystallized from ethanol-water to give 7-benzyloxy-2-naphthoic acid (484 mg, 72%) as a white solid. HRMS (EI) calculated for C18H14O3: 278.0943, found 278.0947.

Workup

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe product is purified by column chromatography (step gradient, 5 to 10% methanol in CH2Cl2)
  7. customThe resulting material is crystallized from ethanol-water

Sources & evidence

ORD record
ord-371734b6b9ca4c608cec735d8d423c8b
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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