Methyl 4-benzyloxy-2-(1-o-tolylethoxy)benzoate → 4-Benzyloxy-2-(1-o-tolylethoxy)benzoic acid

HRID 322925Notes

Reaction equation

HRID 322925 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([O:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[K+].CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH3:21])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22010393Methyl 4-benzyloxy-2-(1-o-tolylethoxy)benzoate

Product 1

HCID 220104904-Benzyloxy-2-(1-o-tolylethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of methyl 4-benzyloxy-2-(1-o-tolylethoxy)benzoate (2.8 g) in 15% KOH in MeOH (50 mL) is refluxed for 3 hours. The solution is evaporated, the residue treated with water, brought to pH 1 with concentrated HCl, extracted with dichloromethane. The extract is dried and evaporated to give 4-benzyloxy-2-(1-o-tolylethoxy)benzoic acid as a colourless solid, m.p. 110-113° C.

Workup

  1. customThe solution is evaporated
  2. additionthe residue treated with water
  3. extractionextracted with dichloromethane
  4. customThe extract is dried
  5. customevaporated

Sources & evidence

ORD record
ord-31ad970e89394ac99e0786053914632d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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