Ethanol → Hydrochloric Acid

HRID 2403236Notes

Reaction equation

HRID 2403236 reaction equation
O=S(Cl)[Cl:3].[CH:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])[CH:6]=1.[CH3:18][CH2:19]O>>[NH2:17][CH:13]([CH2:12][C:7]1[CH:6]=[CH:5][CH:10]=[C:9]([OH:11])[CH:8]=1)[C:14]([O:16][CH2:18][CH3:19])=[O:15].[ClH:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 6950578L-m-tyrosine

Product 2

HCID 313Hydrochloric AcidYield 99%HCID 13890117Ethyl 2-amino-3-(3-hydroxyphenyl)propanoate

Conditions

Temperature
-5 °C

Procedure

To 20 mL of EtOH at −5° C. was added, with stirring, 0.2 mL of SOCl2 slowly. The clear colorless solution was cooled to −5° C. and 510 mg of meta-Tyrosine was added. After 5 min, the resulting solution was refluxed overnight. The solution was concentrated to afford 157 as HCl salt (690 mg, 99%).

Workup

  1. temperaturethe resulting solution was refluxed overnight
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-f1fc64d8783447e0890c3284ea8862b5
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

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