Sodium Hydroxide → 2,5-Bis(benzyloxy)phenol

HRID 31213Notes

Reaction equation

HRID 31213 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[O:23]C(=O)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[OH:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69017220Acetic acid 2,5-bis(benzyloxy)phenyl ester

Product 1

HCID 155069722,5-Bis(benzyloxy)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acetic acid 2,5-bis(benzyloxy)phenyl ester (1.85 g) and 5M sodium hydroxide solution (10.6 ml) in ethanol (11 ml) was heated under reflux for 6.5 hrs. After ethanol was evaporated under reduced pressure the clear solution was made acidic with diluted hydrochloric acid. The precipitated product was collected by filtration, washed with cold water and dried under reduced pressure. Yield is 0.56 g. 1H NMR (DMSO-d6) δ=4.97 (s, 2H), 5.01 (s, 2H), 6.34 (dd, J=3.1, 8.8 Hz, 1H), 6.49(d, J=3.1 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 7.28-7.46 (m, 10H), 9.1 (br s, 1H).

Workup

  1. temperatureunder reflux for 6.5 hrs
  2. customAfter ethanol was evaporated under reduced pressure the clear solution
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with cold water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1109bf4f454b4714b0b8984e3b4cffa9
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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