Sodium Hydroxide → 2-(2-Formyl-3-hydroxyphenoxymethyl)benzoic acid

HRID 485173Notes

Reaction equation

HRID 485173 reaction equation
C([O:4][C:5]1[C:6]([CH:22]=[O:23])=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[OH-].[Na+]>C(O)C>[CH:22]([C:6]1[C:5]([OH:4])=[CH:21][CH:20]=[CH:19][C:7]=1[O:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 202715612-(3-Acetoxy-2-formylphenoxymethyl)benzoic acid

Product 1

HCID 130920992-(2-Formyl-3-hydroxyphenoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of methyl and ethyl 2-(2-methyl-4-benzofuranyloxymethyl) benzoates (1.212 g) was dissolved in absolute ethanol (180 ml) and ozonised in an analogous manner so that described in Example 5(B) to give a mixture of methyl and ethyl esters of 2-(3-acetoxy-2-formylphenoxymethyl)benzoic acid, as an oil. This oil was dissolved in 95% ethanol (15 ml) and treated with 1N sodium hydroxide solution (15 ml) in an analogous manner to that described in Example 6 to give 2-(2-formyl-3-hydroxyphenoxymethyl)benzoic acid, m.p. 218°-219.5° C. (Found: C, 65.91; H, 4.50. C15H12O5 required C, 66.17; H, 4.44%).

Workup

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Sources & evidence

ORD record
ord-007cbeb0d5f449e099ac966a033e9347
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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