Myristic Acid → 2,3-Dimethyl-6-myristoyl-hydroquinone

HRID 1758026Notes

Reaction equation

HRID 1758026 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[CH:5][C:3]=1[OH:4].[C:11](O)(=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClCCCl>[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[C:5]([C:11](=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:3]=1[OH:4]

Participants

4

Reactant 2

HCID 11005Myristic AcidHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 205104672,3-Dimethyl-6-myristoyl-hydroquinone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

93 g of 2,3-dimethyl-hydroquinone and 168 g of myristic acid were dissolved with stirring in 300 ml of 1,2-dichloroethane and heated to 80° C. Boron trifluoride was bubbled through for 4 h and stirring was continued at 80° C. for 2 h. The reaction mixture was poured into 1800 ml of water containing 200 g of dissolved sodium acetate. The organic layer was separated, washed with water and the solvent evaporated in a rotary evaporator. Any precipitate formed during washing should be filtered off and be recrystallized together with the residue after evaporation. The crystallization was effected from a mixture of 1,2-dichloroethane and benzine (1:1 by volume). Yield: 126 g. Melting point: 100° C.

Workup

  1. customBoron trifluoride was bubbled through for 4 h
  2. additionThe reaction mixture was poured into 1800 ml of water containing 200 g of dissolved sodium acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. customthe solvent evaporated in a rotary evaporator
  6. customAny precipitate formed
  7. washduring washing should
  8. filtrationbe filtered off
  9. custombe recrystallized together with the residue
  10. customafter evaporation
  11. customThe crystallization
  12. additionwas effected from a mixture of 1,2-dichloroethane and benzine (1:1 by volume)

Sources & evidence

ORD record
ord-942dac4fcaa340519789b74c4c8fb18a
Source dataset
uspto-grants-1983_02
Patent number
US04371604

Reaction notes

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