Water → (3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethyl phenyl)-3,7,11,15-tetramethyl-3-hexadecanol

HRID 1087297Notes

Reaction equation

HRID 1087297 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH3:14].C([Li])CCC.[O:20]1[C:22]([CH3:39])([CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:21]1.O>O1CCCC1>[CH3:12][O:11][C:6]1[C:7]([CH3:10])=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[C:4]([CH3:14])[C:5]=1[CH2:13][CH2:39][C:22]([CH3:21])([OH:20])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 6017651,4-Dimethoxy-2,3,5,6-tetramethylbenzeneHCID 128109942-Methyl-2-(4,8,12-trimethyltridecyl)oxiraneHCID 178418339Butyllithium

Product 1

HCID 14631374(3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethyl phenyl)-3,7,11,15-tetramethyl-3-hexadecanolYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.8 g (9 mmol) of 2,5-dimethoxy-1,3,4,6-tetramethylbenzene were dissolved in 100 ml of tetrahydrofuran, treated with 1 g (9 mmol) of potassium tert.butylate and subsequently 6 ml (9.5 mmol) of n-butyllithium (1.6 molar) were added dropwise at room temperature. Thereafter, the mixture was stirred at room temperature for 30 minutes, treated dropwise with 2.7 g (9 mmol) of (2RS,6RS,10RS)-1,2-epoxy-2,6,10,14-tetramethylpentadecane and stirred at room temperature for 16 hours. Thereupon. HYFLO and 200 ml of water were added, the mixture was then filtered and washed with water. The residue was stirred up with diethyl ether and sodium sulphate, filtered, washed with diethyl ether and concentrated. There were obtained 3.8 g of (3RS,7RS,11RS)-1-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3,7,11,15-tetramethyl-3-hexadecanol.

Workup

  1. additionwere added dropwise at room temperature
  2. stirringstirred at room temperature for 16 hours
  3. filtrationthe mixture was then filtered
  4. washwashed with water
  5. stirringThe residue was stirred up with diethyl ether and sodium sulphate
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-af7ff8927ccc486c9b71d64fcdc5e0aa
Source dataset
uspto-grants-1991_07
Patent number
US05034546

Reaction notes

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