Acetic Acid → Chromanol

HRID 991853Notes

Reaction equation

HRID 991853 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1[OH:4].C(O)(=O)C.C(C(C)=O)C.[CH2:21]=[CH:22][C:23](=[CH2:25])[CH3:24]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:25][C:23]1([CH3:24])[CH2:22][CH2:21][C:5]2[C:3](=[C:2]([CH3:1])[C:8]([CH3:9])=[C:7]([OH:10])[C:6]=2[CH3:11])[O:4]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6557IsopreneHCID 6569Methyl Ethyl KetoneHCID 12785Trimethylhydroquinone

Product 1

HCID 99479Chromanol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent2×

Procedure

In a 50 ml four-necked flask were charged 2,3,5-trimethylhydroquinone (5.0 g), zinc chloride (0.8 g), acetic acid (0.35 ml), methyl ethyl ketone (4 ml) and toluene (15 ml) and the mixture was heated. At 100° C., a solution of isoprene (2.5 g) in toluene (5 ml) was added dropwise under reflux over 2 hr. After the dropwise addition, the mixture was refluxed for 4 more hours and cooled to room temperature. The reaction mixture was transferred to a partition funnel, and, after washing 3 times with 50 ml of water, the solvent was evaporated to give 6.5 g of an oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux over 2 hr
  3. additionAfter the dropwise addition
  4. temperaturethe mixture was refluxed for 4 more hours
  5. customThe reaction mixture was transferred to a partition funnel
  6. washafter washing 3 times with 50 ml of water
  7. customthe solvent was evaporated
  8. customto give 6.5 g of an oily substance

Sources & evidence

ORD record
ord-a7907a143ea24a6fac3873ebb376a06a
Source dataset
uspto-grants-2002_10
Patent number
US06465548B1

Reaction notes

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