4-Hydroxybenzoic Acid → Salicylic Acid

HRID 1074681Notes

Reaction equation

HRID 1074681 reaction equation
OC1C=CC(C(O)=O)=CC=1.OC1C=C2C(=CC=1)C=C(C(O)=O)C=C2.C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.[OH:42][C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45]([OH:47])=[O:46].[OH:52][C:53]1[CH:62]=[CH:61][C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]=1[C:63]([OH:65])=[O:64]>O>[OH:42][C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45]([OH:47])=[O:46].[OH:52][C:53]1[CH:62]=[CH:61][C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:54]=1[C:63]([OH:65])=[O:64]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 855576-Hydroxy-2-naphthoic acidHCID 9798523Di-n-butyl diacetoxy tinHCID 86738953HCID 86738953, compound

Product 2

HCID 338Salicylic AcidHCID 167902-Hydroxy-1-naphthoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A wholly aromatic copolymer of hydroxybenzoic acid and hydroxynaphthoic acid was prepared by reacting 48.3 g (0.35 mole) of 4-hydroxybenzoic acid with 28.2 g (0.15 mole) of 6-hydroxy 2-naphthoic acid. Dibutyl tin diacetate was used as the catalyst (1800 ppm on total charge). The reaction mixture was heated for 11/2 hrs. at 300° C. and at 320° C. for 30 minutes, by which time it was very viscous. Strong fibers were pulled from the melt. The total yield of water was 17 ml, (94% theory). The isolated polymer had a Tm of 240°, an IV of 6.7 and the FTIR analysis showed a hydroxybenzoic acid/hydroxynaphthoic acid ratio of approximately 65/35.

Workup

  1. temperatureThe reaction mixture was heated for 11/2 hrs
  2. customa Tm of 240°

Sources & evidence

ORD record
ord-c7ab8eb982e14e44b994036741de98db
Source dataset
uspto-grants-1983_07
Patent number
US04393191

Reaction notes

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