2,4-Di-tert-butylphenol → Ethyl 2-(2,4-di-tert-butylphenoxy)caproate

HRID 362693Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].CC[O-].[Na+].Br[CH:21]([CH2:27][CH2:28][CH2:29][CH3:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CCO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][CH:21]([CH2:27][CH2:28][CH2:29][CH3:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

206 g (1 mol) of 2,4-di-tert-butylphenol were melted and heated to 140° C. under nitrogen. 234 g (1.03 mol) of a 30% strength NaOEt solution in EtOH and 245 g (1.1 mol) of ethyl 2-bromocaproate were metered in simultaneously in the course of 1 hour. During the addition, EtOH was distilled off. After the addition, the reaction was ended. The mixture was cooled to 90° C. and 250 ml of water were added. After separation of the phases and washing with 200 ml of water, 347 g of a viscous yellow oil of the following composition (0.3% of ethyl bromocaproate, 0.5% of residual phenol and 98% of ethyl 2-(2,4-di-tert-butylphenoxy)caproate, remained. This corresponds to a yield of 98% of theory, based on the phenol employed.

Workup

customsimultaneously in the course of 1 hour
distillationwas distilled off
additionAfter the addition
temperatureThe mixture was cooled to 90° C.
addition250 ml of water were added
customAfter separation of the phases
washwashing with 200 ml of water, 347 g of a viscous yellow oil of the following composition (0.3% of ethyl bromocaproate, 0.5% of residual phenol and 98% of ethyl 2-(2,4-di-tert-butylphenoxy)caproate

Sources & evidence

ORD record: ord-597adf5c49f94914baf2d2a90bc6c291
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869735

Reaction notes

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