4-(Benzyloxy)-2-ethylbenzaldehyde → 4-(Benzyloxy)-2-ethylbenzoic acid

HRID 499754Notes

Reaction equation

HRID 499754 reaction equation
[O-:1]Cl=O.[Na+].[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[C:15]([CH2:21][CH3:22])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CS(C)=O>[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([OH:1])=[O:18])=[C:15]([CH2:21][CH3:22])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 219496604-(Benzyloxy)-2-ethylbenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 231341484-(Benzyloxy)-2-ethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

An aqueous solution (750 ml) of 85 g of NaClO2 and 90 g of NaH2PO4 is added dropwise with cooling and stirring to 120 g of 4-benzyloxy-2-ethylbenzaldehyde, dissolved in 1 l of DMSO, during which the temperature should not rise above 35° C. The mixture is stirred at RT for a further 3 h, and the precipitate formed is filtered off with suction. The solid is then dissolved in 600 ml of EtOAc, dried and re-evaporated. The residue is crystallised from (Me2CH)2O, giving 4-benzyloxy-2-ethylbenzoic acid; yield 96.2 g (75%); m.p. 132-133°.

Workup

  1. temperaturewith cooling
  2. customrise above 35° C
  3. customthe precipitate formed
  4. filtrationis filtered off with suction
  5. dissolutionThe solid is then dissolved in 600 ml of EtOAc
  6. customdried
  7. customre-evaporated
  8. customThe residue is crystallised from (Me2CH)2O

Sources & evidence

ORD record
ord-3acfdbc683494f1cb3885d6035d98dce
Source dataset
uspto-grants-2010_08
Patent number
US07767716B2

Reaction notes

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