Boron trifluoride → HCID 54411420, compound

HRID 2380023Notes

Reaction equation

HRID 2380023 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][CH2:17][C:18]([CH3:22])=[CH:19][CH2:20][C:8]1[C:2]([CH3:1])=[C:3]([OH:11])[C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[OH:7]

Participants

7

Reactant 3

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

Product 1

HCID 54411420HCID 54411420, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7964ChlorobenzeneSolvent2×HCID 8058HexaneSolvent

Procedure

Trimethylhydroquinone (2.00 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-4-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-4177805e656b499e90452bb645989154
Source dataset
uspto-grants-1994_11
Patent number
US05364946

Reaction notes

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