Ethanol → 5-(Benzyloxy)-2-hydroxybenzaldehyde

HRID 466170Notes

Reaction equation

HRID 466170 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[CH2:22]([OH:24])C>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([CH:14]=1)[CH:22]=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 7638MonobenzoneHCID 14798Sodium Hydroxide

Product 1

HCID 8783625-(Benzyloxy)-2-hydroxybenzaldehyde

Conditions

Temperature
70 °C

Procedure

The starting material is prepared as follows: 4-Benzyloxyphenol (20 g, 0.1 mol) is dissolved in 24 ml of ethanol and 120 ml of 20% aqueous sodium hydroxide (24 g NaOH, 0.6 mol), and heated at 70° C. To this is added chloroform (23.9 g, 0.2 mol) dropwise and the mixture is stirred for 3.5 hours at 70° C. The mixture is cooled and evaporated. The residue is then treated with conc. HCl until the pH of the solution is 1 to 3. The mixture is extracted with ether three times, and the combined organic layer is dried (MgSO4), evaporated and purified by silica gel chromatography (5% ethyl acetate/hexane) to give 5-benzyloxy-2-hydroxybenzaldehyde as a pale yellow, crystalline solid, m.p. 94°-96° C.

Workup

  1. customThe starting material is prepared
  2. temperatureThe mixture is cooled
  3. customevaporated
  4. additionThe residue is then treated with conc. HCl until the pH of the solution
  5. extractionThe mixture is extracted with ether three times
  6. dry with materialthe combined organic layer is dried (MgSO4)
  7. customevaporated
  8. custompurified by silica gel chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d8376cd991ed4be19b732944861ad40c
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

Loading…