tert-Butanol → Tert-butyl 3-oxooctadecanoate

HRID 236473Notes

Reaction equation

HRID 236473 reaction equation
[CH3:1][C:2]1([CH3:27])[O:7][C:6](=[O:8])[C:5](=[C:9]([OH:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])C(=O)O1.[C:28](O)(C)(C)C>C1C=CC=CC=1>[O:25]=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][C:6]([O:7][C:2]([CH3:1])([CH3:27])[CH3:28])=[O:8]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 546979555-(1-Hydroxyhexadecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 16110963Tert-butyl 3-oxooctadecanoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,2-Dimethyl-5-(1-hydroxyhexadecylidene)-1,3-dioxane-4,6-dione (200 g) and tert-butyl alcohol (170 g) were refluxed in benzene (1 l) for 4 hours. Evaporation of the solvent gave crude tert-butyl 3-oxooctadecanoate (185 g) as an oil.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-93fbdca666374d4cac0f8cdb6ca9fc39
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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