Methanol → Benzoic acid, 4-octyl-, methyl ester

HRID 1167044Notes

Reaction equation

HRID 1167044 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:18][OH:19]>CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[CH2:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:19][CH3:18])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 887MethanolHCID 170865Benzoyl chloride, 4-octyl-

Product 1

HCID 104715Benzoic acid, 4-octyl-, methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

4-Octylbenzoyl chloride (obtained by reacting 4-octylbenzoic acid with thionyl chloride) is esterified with methanol in the presence of an equimolar amount of triethylamine and 0.1 mol % of DMAP. Customary work-up followed by purification by distillation affords methyl 4-octylbenzoate as a colorless liquid, b.p. 112° C./0.25 mbar.

Workup

  1. distillationCustomary work-up followed by purification by distillation

Sources & evidence

ORD record
ord-e4739e1df08249cc8e15da5aefd0e48e
Source dataset
uspto-grants-2003_09
Patent number
US06616989B1

Reaction notes

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