Boron trifluoride → HCID 54411420, compound

HRID 1033591Notes

Reaction equation

HRID 1033591 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 62.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7964ChlorobenzeneSolventHCID 8058HexaneSolvent

Procedure

Trimethylhydroquinone (2.00 g, 14 mmol) 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 92.42 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 ml) and dried at 40° C./20 mbar for 8 hours. 2.24 g (62.6 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. washthe filtrate was washed with chlorobenzene (10 ml)
  3. customdried at 40° C./20 mbar for 8 hours

Sources & evidence

ORD record
ord-9d2ab99d6e484007b81fdb14ebf446ad
Source dataset
uspto-grants-1994_05
Patent number
US05310953

Reaction notes

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