Ethanol → 2-Benzyloxybenzoic acid

HRID 38640

Reaction equation

HRID 38640 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CCO>O>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 345928Ethyl 2-(benzyloxy)benzoate

Product 1

HCID 18105812-Benzyloxybenzoic acidYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 73 (4.0 g, 15.6 mmol) in H2O (150 ml) were added NaOH (3.1 g, 78.0 mmol) and EtOH (5 ml). The mixture was reflux for 12 h, and cooled to 25° C. The solid was filtered out and the filtrate was acidified with 2N HCl. The precipitate was collected and washed with H2O. The crude product was recrystallized from to give 78 as white solid. (3.0 g, 13.2 mmol). Yield: 84.6%; mp 73-75° C.; MS (EI, 70 eV): m/z 228.3 (M+); 1H-NMR (CDCl3, 200 MHz): δ 5.27 (s, 2H), 7.08-7.54 (m, 8H), 6.93 (dd, J=8.0, 1.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 165.43, 157.40, 135.02, 134.34, 133.88, 129.16, 127.92, 122.44, 118.09, 113.11, 72.23; Anal. Calcd for C14H12O3: C, 73.67; H, 5.30.

Workup

  1. temperatureThe mixture was reflux for 12 h
  2. filtrationThe solid was filtered out
  3. customThe precipitate was collected
  4. washwashed with H2O
  5. customThe crude product was recrystallized from

Sources & evidence

ORD record
ord-11b9b0ab40304925a3d101c2731ff662
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Linked notes

Loading…