m-Chloroperbenzoic acid → HCID 54458043, compound

HRID 1576997Notes

Reaction equation

HRID 1576997 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])=[C:13]([CH3:15])[CH3:14])=[CH:3][CH2:4][OH:5].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[O:26]1[C:13]([CH3:15])([CH3:14])[C:12]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:17])=[CH:8][CH2:7][CH2:6][C:2]([CH3:1])=[CH:3][CH2:4][OH:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53812327HCID 53812327, compound

Product 1

HCID 54458043HCID 54458043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 23.6 g. of 3,7,10,11-tetramethyl-2,6,10-dodecatrien-1-ol in 500 ml. of methylene chloride, there was added under ice cooling 22.6 g. of m-chloroperbenzoic acid (79% by weight water solution). This addition was carried out portionwise. After this addition, the mixture was agitated for 2 hours at 0°C. After this period, the reaction mixture was diluted with 1,000 ml. of diethyl ether and washed with ice cold 1N aqueous sodium hydroxide and a saturated sodium chloride solution. After washing, the reaction mixture was dried over sodium sulfate and evaporated. By chromatography on Kieselgel, there was obtained 10,11-epoxy-3,7,10,11-tetramethyl-2,6-dodecadien-1-ol, b.p. 104°- 107°C./0.02 mmHg; nD20 = 1.4867.

Workup

  1. additionThis addition
  2. additionAfter this addition
  3. waitAfter this period
  4. additionthe reaction mixture was diluted with 1,000 ml
  5. washof diethyl ether and washed with ice cold 1N aqueous sodium hydroxide
  6. washAfter washing
  7. dry with materialthe reaction mixture was dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-ee8cab73eb404a659a10b983fb23b27d
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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