Sodium Hydroxide → HCID 13375422, compound

HRID 1762006Notes

Reaction equation

HRID 1762006 reaction equation
[CH2:1]([NH:8][C:9]([CH3:21])([CH2:12][CH2:13][O:14]C1CCCCO1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH2:1]([NH:8][C:9]([CH3:21])([CH2:12][CH2:13][OH:14])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15599314HCID 15599314, compound

Product 1

HCID 13375422HCID 13375422, compound

Procedure

The crude 2-benzylamino-2-methyl-4-((tetrahydro-2H-pyran-2-yl)oxy)butanol (12D, 80.1 g, 0.273 mol) was dissolved in 3N NCl (128 mL). After 5 min the mixture was washed with Et2O (200 mL). The aqueous solution was concentrated by rotary evaporation to give a thick oil which was cooled and basified with excess 50% NaOH. The oily amine which formed was extracted with Et2O (3×200 mL). The Et2O extracts were combined and concentrated to give 63.6 g of a thick oil. Distillation gave 49.8 g (94%) of 2-benzylamino-2-methyl-1,4-butanediol as a pale yellow oil (bp 168°-170°/0.35 mm) (C,H,N).

Workup

  1. washAfter 5 min the mixture was washed with Et2O (200 mL)
  2. concentrationThe aqueous solution was concentrated by rotary evaporation
  3. customto give a thick oil which
  4. temperaturewas cooled

Sources & evidence

ORD record
ord-a510c3abbe534074a5ca780c2b9c223b
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Reaction notes

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