Water → 2-(Benzyloxy)-5-formylbenzoic acid

HRID 1623717Notes

Reaction equation

HRID 1623717 reaction equation
[OH-].[Li+].O.[CH:4]([C:6]1[CH:7]=[CH:8][C:9]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:10]([CH:21]=1)[C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:5]>O1CCCC1.CO>[CH:4]([C:6]1[CH:7]=[CH:8][C:9]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:10]([CH:21]=1)[C:11]([OH:13])=[O:12])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Product 1

HCID 9698702-(Benzyloxy)-5-formylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (207 mg, 8.66 mmol) and water (2.5 ml) were added to a solution of phenylmethyl 5-formyl-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in description 96) (1 g, 2.89 mmol) in tetrahydrofuran (10 ml) and methanol (2.5 ml). The mixture was stirred overnight. The tetrahydrofuran/methanol was removed in vacuo and the remaining aqueous solution was acidified to pH=1 and extracted with ethyl acetate (3×20 ml). The solvent was removed in vacuo to yield the title compound as a white solid. 1.1 g.

Workup

  1. customThe tetrahydrofuran/methanol was removed in vacuo
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eac04863cf2541cebec2dcaa4cde719d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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