Water → 1-Naphthaleneacetic Acid

HRID 1439797Notes

Reaction equation

HRID 1439797 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:13][O-:14].[Na+].[OH2:16].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CO.[Mn]>[C:3]1([CH2:2][C:13]([OH:16])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 68451-ChloromethylnaphthaleneHCID 24489Sodium DithioniteHCID 10942334Sodium Methoxide

Product 1

HCID 68621-Naphthaleneacetic AcidYield 6.5%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 887MethanolSolvent

Procedure

In the manner described in Example 1, 58 g of alphachloromethylnaphthalene was reacted with CO together with 78 g of a 24 wt-% sodium methylate solution in methanol, 12 g CoCl2.6 H2O, 6 g manganese and 1 g Na2S2O4. The usual processing yielded 35 g naphthyl-(1)-acetic acid methyl ester (yield 53%) and 7 g of alpha-naphthylacetic acid (yield 6.5%).

Sources & evidence

ORD record
ord-7713ff8044e343a8adab6d3e253fb7c7
Source dataset
uspto-grants-1977_11
Patent number
US04060690

Reaction notes

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