Diethyl Ether → Hydroxyphenylacetic acid

HRID 648381Notes

Reaction equation

HRID 648381 reaction equation
[C:1]1([O:7]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:10][C:11]1[CH:16]=CC(CC#N)=CC=1.I.CC[O:23]CC>>[OH:7][C:1]1[CH:2]=[CH:3][C:4]([CH2:16][C:11]([OH:10])=[O:23])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 7519AnisoleHCID 24841Hydrogen iodideHCID 66031Benzeneacetonitrile, 4-methoxy-2×

Product 1

HCID 127Hydroxyphenylacetic acid

Procedure

A method in which anisole, which is a starting material, is subjected to chloromethylation and a cyanation to be thereby converted to 4-methoxyphenylacetonitrile (Organikum, Berlin, nine edit., p. 363); and the resultant 4-methoxyphenylacetonitrile is saponified to produce an acid, which is subsequently treated with hydriodic acid to eliminate an ether, whereby 4-hydroxyphenylacetic acid is obtained as the desired product (J. Org. Chem., Vol. 22, 1957, p. 1577).

Workup

  1. customto produce an acid, which

Sources & evidence

ORD record
ord-ed41455aa2ba40a3bbadc40d3a4c4ba8
Source dataset
uspto-grants-1983_10
Patent number
US04412082

Reaction notes

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