2-tert-Butyl-6-methylphenol → HCID 19003350, compound

HRID 2259324Notes

Reaction equation

HRID 2259324 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[OH:25])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([C:6]1[CH:7]=[C:8]([C:9](=[O:10])[CH2:22][CH2:23][CH2:18][C:19]([C:22]2[CH:21]=[C:20]([CH3:24])[C:19]([OH:25])=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:23]=2)=[O:25])[CH:21]=[C:20]([CH3:24])[C:5]=1[OH:12])([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 166782-tert-Butyl-6-methylphenolHCID 17887Pentanedioyl dichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19003350HCID 19003350, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

27 g (200 mmol) of aluminium chloride, 6.5 ml (50 mmol) of glutaric acid chloride and 250 ml of methylene chloride are initially introduced into a 500 ml three-necked round-bottomed flask. The suspension is cooled to -60° C. and a solution of 18 g (110 mmol) of 2-tert-butyl-6-methylphenol in 30 ml of methylene chloride is added dropwise in the course of about 30-40 minutes. The hydrochloric acid gas which evolves is collected in water. The reaction mixture is stirred at -50° C. for 30 minutes and is then poured onto ice. After addition of 20 ml of concentrated hydrochloric acid, the mixture is stirred for about 10 minutes. The phases are separated and the organic phase is dried over sodium sulfate and freed from the solvent on a rotary evaporator. The 20 g of crude product thus obtained are purified by column chromatography (SiO2, toluene/ethyl acetate 19:1). 12 g (56% of theory) of 1,5-di(3'-tert-butyl-5'-methyl-4'-hydroxyphenyl)-1,5-pentanedione of melting point 156°-158° C. result. The vibration band of the CO groups in the infra-red spectrum appears at 1663.7 cm-1.

Workup

  1. customThe hydrochloric acid gas which evolves is collected in water
  2. additionis then poured onto ice
  3. additionAfter addition of 20 ml of concentrated hydrochloric acid
  4. stirringthe mixture is stirred for about 10 minutes
  5. customThe phases are separated
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. customfreed from the solvent on a rotary evaporator
  8. customThe 20 g of crude product thus obtained
  9. customare purified by column chromatography (SiO2, toluene/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-ead27edd87434705a39047383d2efede
Source dataset
uspto-grants-1995_12
Patent number
US05473003

Reaction notes

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