Water → HCID 53793676, compound

HRID 1732258Notes

Reaction equation

HRID 1732258 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][C:14]([CH3:18])=[CH:15][CH2:16]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:22]O.O.CC[O:27][CH2:28][CH3:29]>[Cl-].[Na+].O>[CH2:1]([O:8][CH2:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][C:14]([CH3:18])=[CH:15][CH2:16][CH2:22][C:28](=[O:27])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 23721981Sodium hydroxide methanolHCID 53665877HCID 53665877, compound

Product 1

HCID 53793676HCID 53793676, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The β-ketoester derived from 8-benzyloxy-3,7-dimethyl-2-octenyl chloride (25.2 g, 67.5 mM) is treated with 2 N sodium hydroxide/methanol (675 ml) and after 10 minutes water (675 ml) is added. The reaction mixture is heated at reflux for 3 hours. The solvent is removed in vacuo and the residue obtained is treated with ether and brine. The layers are separated, the aqueous phase is extracted with ether, and the combined extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give the crude product (16 g). Purification over silica gel using 5% ethyl acetate/hexane as the eluent gives 1-benzyloxy-2,6-dimethyl-10-oxo-undec-6-ene (12.4 g, 61%) with a 83/17 E/Z isomer ratio by gas chromatography:

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 3 hours
  4. customThe solvent is removed in vacuo
  5. customthe residue obtained
  6. customThe layers are separated
  7. extractionthe aqueous phase is extracted with ether
  8. washthe combined extracts are washed with brine
  9. dry with materialdried (Na2SO4)
  10. customThe solvent is removed in vacuo
  11. customto give the crude product (16 g)
  12. customPurification over silica gel using 5% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-857e785429db42c387897ecfa50b625d
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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