Sodium Hydroxide → HCID 20062998, compound

HRID 709539Notes

Reaction equation

HRID 709539 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C(O)C>[CH2:15]([O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:22])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10935464HCID 10935464, compound

Product 1

HCID 20062998HCID 20062998, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-benzyloxy-phthalic acid dimethyl ester (1.64 g, 5.50 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 1 h and cooled to room temperature. The solvent was removed under vacuum and the residue was dissolved in water (100 mL), washed with CH2Cl2 (2×100 mL) and acidified with 6N HCl to pH 1-2. The precipitate was filtered and washed with water (100 mL) to give 3-benzyloxy-phthalic acid as a white solid (1.10 g, 74% yield); 1H NMR (DMSO-d6) δ 5.20 (s, 2H), 7.29-7.51 (m, 8H), 13.02 (br, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in water (100 mL)
  5. washwashed with CH2Cl2 (2×100 mL)
  6. filtrationThe precipitate was filtered
  7. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-5cf13d1175df4d6681c97460c2cae004
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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