2,3,5-Trimethylphenol → Ethyl 6-(2'-hydroxy-3',4',6'-trimethylbenzoyl)hexanoate

HRID 1390558Notes

Reaction equation

HRID 1390558 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:17]>>[OH:10][C:3]1[C:2]([CH3:1])=[C:7]([CH3:8])[CH:6]=[C:5]([CH3:9])[C:4]=1[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:17]

Participants

4

Reactant 3

HCID 127692,3,5-Trimethylphenol2×HCID 543232Ethyl 6-(Chloroformyl)hexanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12906130Ethyl 6-(2'-hydroxy-3',4',6'-trimethylbenzoyl)hexanoate

Procedure

2,3,5-Trimethylphenol (formula VII wherein R=H3C, X=H, Y=OH)(0.9 part), aluminum chloride (2.1 parts) and ethyl 6-chloroformylhexanoate (1.3 part) were treated as in Example 1 (1). The procedure provided colorless needles of ethyl 6-(2'-hydroxy-3',4',6'-trimethylbenzoyl)hexanoate (formula II-1 wherein R=H3C, X=H, Y=OH, n=5, in the form of ethyl ester) (1.5 part) melting at 47°-48° C.

Sources & evidence

ORD record
ord-aa94e21d6f0441b28f19c7dec552c92e
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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