Citric Acid → 1-(Benzyloxy)-2-naphthoic acid

HRID 70010Notes

Reaction equation

HRID 70010 reaction equation
C1COCC1.[OH-].[Na+].C([O:15][C:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:17])C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH2:29]([O:28][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[C:16]([OH:17])=[O:15])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 539440891-Benzyloxy-naphthalene-2-carboxylic acid benzyl ester

Product 1

HCID 190319371-(Benzyloxy)-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Method slightly modified, THF (30 mL) instead of MeOH and 5M NaOH (32 mL) were added to the rbf containing compound 1-Benzyloxy-naphthalene-2-carboxylic acid benzyl ester (1.40 g, 3.80 mmol). A condenser was added and the mixture was refluxed for 9 hours. The mixture was diluted with H2O (100 mL) and citric acid (17.70 g, 92.12 mmol) was added to pH-4. Extracted with CH2Cl2 (3×100 mL), washed with H2O (2×150 mL) and saturated NaCl (1×150 mL). NMR showed final product with small percent of starting material. Purification was achieved by recrystallization in hexanes (2×20 mL). Solvent removed under pressure and concentrated in vacuo. Yield: 0.652 g of white crystals (62%). 1H NMR (400 MHz, CDCl3) δ 5.24 (s, 2H), δ 7.43-7.54 (m, 3H), δ 7.61-7.68 (m, 2H), δ 7.75 (d, J=8.7 Hz, 1H), δ 7.93 (dd, J=7.3 Hz, 1 Hz, 1H), δ 8.10 (d, J=8.7 Hz, 1H), δ 8.25 (d, J=7.8 Hz, 1H).

Workup

  1. additionA condenser was added
  2. temperaturethe mixture was refluxed for 9 hours
  3. additionwas added to pH-4
  4. extractionExtracted with CH2Cl2 (3×100 mL)
  5. washwashed with H2O (2×150 mL) and saturated NaCl (1×150 mL)
  6. customPurification
  7. customwas achieved by recrystallization in hexanes (2×20 mL)
  8. customSolvent removed under pressure
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3ed80169c2948a0960638cfcc4a9a74
Source dataset
uspto-grants-2014_09
Patent number
US08822515B2

Reaction notes

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