Water → HCID 13633545, compound

HRID 978912Notes

Reaction equation

HRID 978912 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].Cl[CH2:13][CH:14]=[C:15]([CH3:35])[CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:29])[CH3:28].CCCCCC.O>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:35][C:15]1([CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:29])[CH3:28])[CH2:14][CH2:13][C:8]2[C:6](=[C:5]([CH3:9])[C:4]([CH3:10])=[C:3]([OH:11])[C:2]=2[CH3:1])[O:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 12785TrimethylhydroquinoneHCID 54100633HCID 54100633, compound

Product 1

HCID 13633545HCID 13633545, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
30 °C

Procedure

Trimethylhydroquinone (8.4 g), 1,7,11,15-tetrachloro-3,7,11,15-tetramethyl-hexadec-2-ene (22 g) and acetic acid (30 cc) are introduced into a 250 cc reactor. A solution of zinc chloride (1.5 g) in anhydrous acetic acid (15 cc) is then added over the course of 10 minutes. The temperature rises from 25° to 30° C. The reaction mixture is stirred for 2 hours at 30° C. and is then poured into a mixture of hexane (100 cc) and water (100 cc). The organic phase is removed by decanting, and washed with a mixture (100 cc) of methanol and water (50:50 by volume). A white precipitate forms in the hexane phase; it is filtered off and washed with a mixture (50 cc) of methanol and water (50:50 by volume). After drying under reduced pressure, 2,5,7,8-tetramethyl-2-(4',8',12'-trichloro-4',8',12'-tri-methyl-tridecyl)-chroman-6-ol (14.3 g) is obtained in the form of white crystals melting at 102°-104° C. The yield is 62%.

Workup

  1. customrises from 25° to 30° C
  2. customThe organic phase is removed
  3. customby decanting
  4. washwashed with a mixture (100 cc) of methanol and water (50:50 by volume)
  5. filtrationit is filtered off
  6. washwashed with a mixture (50 cc) of methanol and water (50:50 by volume)
  7. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-7e3b43e16daa47cc934f5bfa467398c1
Source dataset
uspto-grants-1987_05
Patent number
US04665244

Reaction notes

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