Boron trifluoride → HCID 54360411, compound

HRID 1464430Notes

Reaction equation

HRID 1464430 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].B(F)(F)F.[Cl:16][CH2:17][C:18]([CH3:22])(O)[CH:19]=[CH2:20]>ClC1C=CC=CC=1.CCCCCC.C(OCC)C>[Cl:16][CH:17]([C:8]1[C:2]([CH3:1])=[C:3]([OH:11])[C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[OH:7])[C:18]([CH3:22])=[CH:19][CH3:20]

Participants

7

Reactant 3

HCID 6356Boron trifluoride2×HCID 12785TrimethylhydroquinoneHCID 117891931-chloro-2-methyl-3-buten-2-ol

Product 1

HCID 54360411HCID 54360411, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7964ChlorobenzeneSolvent2×HCID 8058HexaneSolvent

Procedure

Trimethylhydroquinone (2.01 g, 14 mol) was suspended at room temperature in a mixture of chlorobenzene (10 ml) and hexane (5 ml). Boron trifluoride diethyl ether complex (3.60 ml of a 48 percent strength solution of boron trifluoride in diethyl ether, 1.95 g of boron trifluoride, 28 mmol) was then added in the course of 15 min. 1-Chloro-2-methylbut-3-en-2-ol (2.42 g, 20 mmol) was then added dropwise in the course of 15 min. After 30 min., the reaction mixture was filtered, and the filtrate was washed with chlorobenzene (10 mol) and dried at 40° C./20 mbar for 8 hours. 2.24 g (62.9 percent) of 2-(1-chloro-2-methylbut-2-en-yl)-1,4-dihydroxy-3,5,6-trimethylbenzene were obtained. The melting point of the product Was 118 to 122° C. (decomposition). Other data regarding the product was:

Workup

  1. filtrationthe reaction mixture was filtered
  2. customdried at 40° C./20 mbar for 8 hours

Sources & evidence

ORD record
ord-124166a561ba48c1b821df1b0a7eb9b3
Source dataset
uspto-grants-1994_04
Patent number
US05304663

Reaction notes

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