Epichlorohydrin → 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide

HRID 2288261Notes

Reaction equation

HRID 2288261 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>O>[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:14][C@H:16]2[O:18][CH2:17]2)=[CH:7][CH:6]=1)(=[O:10])[NH2:11]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide2×HCID 86986(4-Hydroxyphenyl)acetamide

Product 1

HCID 7852594-[(2S)-2-OxiranylMethoxy]benzeneacetaMideYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

p-Hydroxyphenyl acetamide (30.02 g) was dissolved in 106.5 g of water containing sodium hydroxide (9.6 g) and the solution was cooled to 5° C. Epichlorohydrin (18.5 g, 98.9% e.e.) was dropped in the solution over a period of 10 minutes under stirring at the same temperature and the solution was stirred for 24 hours. Sodium hydroxide (2.4 g) was added thereto and the mixture was stirred for 5 hours. Resulting crystals were filtrated by suction, washed with water and dried in vacuo to give crude (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane (39.8 g). The optical purity of it was 91.2% e.e. by measurement of Chiral column OD (Daisel Chemical Industries Ltd.).

Workup

  1. stirringthe solution was stirred for 24 hours
  2. stirringthe mixture was stirred for 5 hours
  3. customResulting crystals
  4. filtrationwere filtrated by suction
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-78491c098fb94137ac5118a380657d56
Source dataset
uspto-grants-2000_07
Patent number
US06087512

Reaction notes

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