Neopentyl alcohol → HCID 545965, compound

HRID 1380114Notes

Reaction equation

HRID 1380114 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH3:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13]>C1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 6404Neopentyl alcoholHCID 898486-Bromohexanoyl chloride

Product 1

HCID 545965HCID 545965, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6-bromohexanoyl chloride (10.0 g, 0.047 mol) and 2,2-dimethylpropanol (4.96 g, 0.056 mol) in benzene (100 ml) was heated under reflux for 2 hours. The solvent was evaporated off under reduced pressure and the residue was dissolved in dichloromethane (200 ml), washed with aqueous sodium hydroxide (2M, 50 ml), water (50 ml) and dried (Na2SO4). The solvent was evaporated off under reduced pressure to give the crude product which was further purified by column chromatography (alumina, dichloromethane) to give neopentyl 6-bromohexanoate as a colourless oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (200 ml)
  4. washwashed with aqueous sodium hydroxide (2M, 50 ml), water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated off under reduced pressure
  7. customto give the crude product which
  8. customwas further purified by column chromatography (alumina, dichloromethane)

Sources & evidence

ORD record
ord-3156752c4bdd44f989541f8618d566ec
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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