Sulfuric Acid → (+)-4-(2'-Methylbutyl)phenyl 2-chloro-4-hydroxybenzoate

HRID 2048952Notes

Reaction equation

HRID 2048952 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][CH:13]([CH2:22][CH3:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=1.S(=O)(=O)(O)O.B(O)(O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:13]([CH3:12])[CH2:22][CH3:23])=[CH:20][CH:19]=1)=[O:5]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 918212-Chloro-4-hydroxybenzoic acidHCID 22137140(+)4-(2'-Methylbutyl)phenol

Product 1

HCID 20439632(+)-4-(2'-Methylbutyl)phenyl 2-chloro-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This esterficiation may be carried out by the method described by Lowrance (Tet. Lett. 1971, 3453). The reactants (2-chloro-4-hydroxybenzoic acid and (+)4-(2'-methylbutyl)phenol in equimolar amounts) are dissolved in toluene and heated in a Dean and Stark apparatus together with catalytic amounts of sulphuric acid and boric acid. After crystallisation from ethanol/water, the product has the m.p. 142° C.

Workup

  1. customAfter crystallisation from ethanol/water

Sources & evidence

ORD record
ord-8cb624d8ecf341c2b592a435a7dc4629
Source dataset
uspto-grants-1980_04
Patent number
US04195916

Reaction notes

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