Benzyl Alcohol → HCID 22759231, compound

HRID 329295Notes

Reaction equation

HRID 329295 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([CH:14]([CH2:26][CH2:27][CH2:28][CH:29]1[O:31][CH2:30]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:13])[CH3:12]>O>[C:11]([CH:14]([CH2:26][CH2:27][CH2:28][CH:29]([OH:31])[CH2:30][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)=[O:22])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 22759269HCID 22759269, compound

Product 1

HCID 22759231HCID 22759231, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (0.04 mole) is added in portions with stirring to benzyl alcohol (25 ml.). To the resulting solution, ethyl 8-acetyl-12,13-epoxytridecanoate (0.02 mole) is added and the mixture allowed to stand 18 hours at 55°-60°. The reaction mixture is then cooled and treated with water. The organic layer is separated and dried over magnesium sulfate. Excess benzyl alcohol is removed by distillation in vacuo by means of the rotary evaporator at oil pump pressure. The residue consists mainly of the title compound and is used in the next step without purification.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. customExcess benzyl alcohol is removed by distillation in vacuo by means of the rotary evaporator at oil pump pressure
  5. customis used in the next step without purification

Sources & evidence

ORD record
ord-5ad1cb0b87664dcb971bafe4154b64bc
Source dataset
uspto-grants-1977_04
Patent number
US04020177

Reaction notes

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