Boron trifluoride → 2,3-Dimethyl-6-myristoyl-hydroquinone

HRID 224467

Reaction equation

B(F)(F)F.[CH3:5][C:6]1[C:12]([CH3:13])=[C:11]([OH:14])[CH:10]=[CH:9][C:7]=1[OH:8].[C:15](O)(=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C([O-])(=O)C.[Na+]>C1C=CC=CC=1.C(Cl)Cl>[CH3:5][C:6]1[C:12]([CH3:13])=[C:11]([OH:14])[CH:10]=[C:9]([C:15](=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7]=1[OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

Boron trifluoride was introduced with vigorous refluxing (bath temperature 50° C.) into a mixture of 138 g (1 mole) of 2,3-dimethylhydroquinone, 370 g (1.62 moles) of myristic acid and 700 ml of methylene chloride until saturation. After standing overnight the reaction mixture was decomposed by pouring into 3 l of a 10% by weight sodium acetate solution with stirring. The methylene chloride was evaporated by means of steam. The residual oily layer solidified after cooling to a melt cake that was isolated by decantation. It was melted up and added with stirring to 2 l of high-boiling benzine. The precipitate was filtered with suction and washed with benzine (boiling range: 50°-75° C.). After being dried the precipitate was stirred with acetonitrile and filtered with suction.

Workup

customThe methylene chloride was evaporated by means of steam
temperatureafter cooling to a melt cake that
customwas isolated by decantation
additionadded
filtrationThe precipitate was filtered with suction
washwashed with benzine (boiling range: 50°-75° C.)
customAfter being dried the precipitate
stirringwas stirred with acetonitrile
filtrationfiltered with suction

Sources & evidence

ORD record: ord-07d8b452c2364852bfe5eaac08c6343c
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04232107

Linked notes

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