Hydrochloric Acid → 6-Phenoxy-o-cresol

HRID 1164055

Reaction equation

HRID 1164055 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1N.Cl.N([O-])=[O:18].[Na+].F[B-](F)(F)F.[H+]>C(O)(=O)C.O>[O:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[C:3]=1[OH:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 28118Tetrafluoroboric acidHCID 122900472-Methyl-6-phenoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 227346816-Phenoxy-o-cresolYield 38.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-methyl-6-phenoxyaniline (19.3 g) in a mixture of conc. hydrochloric acid (17 ml) and water (60 ml), aqueous solution (10 ml) of sodium nitrite (6.7 g) and 42% fluoroboric acid (19 ml) were treated in a similar manner to that of Example 14-(1). The resultant diazonium salt was treated with acetic acid (400 ml) in a similar manner to that of Example 14-(1) to give oily 6-phenoxy-o-cresol (7.5 g).

Workup

  1. additionwere treated in a similar manner to that of Example 14-(1)

Sources & evidence

ORD record
ord-31fa700f4dd1470992ca34c7a0fcc8a1
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Linked notes

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