Ethanol → HCID 11022381, compound

HRID 232396Notes

Reaction equation

HRID 232396 reaction equation
[CH3:1][C@@:2]([OH:31])([CH2:15][CH2:16][CH2:17][CH:18]([CH3:30])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.C(O)C.[OH-].[Na+]>O>[O:31]1[C@:2]([CH3:1])([CH2:15][CH2:16][CH2:17][CH:18]([CH3:30])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 11037794HCID 11037794, compound

Product 1

HCID 11022381HCID 11022381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.52 g (3.3 mmol) of (2R,6RS,10RS)-2,6,10,14-tetramethyl-1-tosyloxy-2-pentadecanol were dissolved ind 20 ml of ethanol. 2 ml of sodium hydroxide solution (50%) were then added and the mixture was stirred for 16 hours. Subsequently, 50 ml of water were added and the mixture was stirred up with HYFLO. The suspension was then filtered and washed with water. The residue was triturated with diethyl ether, dried over sodium sulphate, filtered and concentrated. There was obtained (2R,6RS,10RS)-1,2-epoxy-2,6,10,14-tetramethylpentadecane with [α]D20 =-0.21° (c=2% in CHCl3).

Workup

  1. stirringthe mixture was stirred up with HYFLO
  2. filtrationThe suspension was then filtered
  3. washwashed with water
  4. customThe residue was triturated with diethyl ether
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd103cbbe42444ceb2932bf0ad04951d
Source dataset
uspto-grants-1989_07
Patent number
US04851585

Reaction notes

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