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

HRID 1455018Notes

Reaction equation

HRID 1455018 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-cddc7fa6bc7b499894c939376ca5a3e7
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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