Acetic Acid → Phenol, 2-bromo-4-propyl-

HRID 1277852Notes

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=C[C:5]=1O)[CH2:2]C.[Br:11]Br.[C:13]([OH:16])(=O)[CH3:14]>>[Br:11][C:2]1[CH:1]=[C:4]([CH2:9][CH2:8][CH3:7])[CH:5]=[CH:14][C:13]=1[OH:16]

Participants

Reactant 3

HCID 176Acetic Acid2×

HCID 125702-Propylphenol

HCID 24408Bromine

Product 1

HCID 18795377Phenol, 2-bromo-4-propyl-

Conditions

Temperature: 60 °C

Procedure

Following step (4) of the reaction system, 20.5 g (0.15 mol) of a commercial grade n-propylphenol was dissolved in 100 ml of glacial acetic acid and heated to 40° C. with 24.5 g (0.153 mol) of bromine dissolved in 50 ml of glacial acetic acid. The mixture was stirred and heated at 60° C. for 4 hours. After the reaction was complete, the acetic acid was removed by distillation and the remaining liquid was distilled under reduced pressure to yield 2 mmHg of 2-bromo-4-n-propylphenol having a boiling point of 73° to 76° C. The 2-bromo-4-n-propylphenol was cyanized in accordance with step (5) as in Example 1 to yield 2 mmHg of 2-cyano-4-n-propylphenol (hereinafter referred to as material G) having a boiling point of 110° C. Materials F and G are esterified in accordance with step (6) as in Example 1 to yield the desired (2'-cyano-4'-propyl) phenol-3-chloro-4-n-heptyloxybenzoate. The benzoate had a melting point of 43.5° C. and an infrared absorption spectrum as illustrated in FIG. 10.

Workup

customthe acetic acid was removed by distillation
distillationthe remaining liquid was distilled under reduced pressure

Sources & evidence

ORD record: ord-36738ffc8b0b418891bb3b71718e3585
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04279771

Reaction notes

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