Hydrochloric Acid → HCID 57001459, compound

HRID 569229Notes

Reaction equation

HRID 569229 reaction equation
[I:1][CH:2]([O:5][C:6](=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]C(=O)C)=[CH:10][CH:9]=1)[C:3]#[CH:4].C(N)CCC.C(OCC)C.Cl>O1CCOCC1>[I:1][CH:2]([O:5][C:6](=[O:18])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[C:3]#[CH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8007ButylamineHCID 57168597HCID 57168597, compound

Product 1

HCID 57001459HCID 57001459, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At room temperature, 15 g (0.042 mole) of 4-acetoxyphenylacetic acid iodopropargyl ester (prepared according to B) and 3.1 g (0.042 mole) of n-butylamine was stirred in 15 ml dioxan for 18 hours. The reaction mixture was distributed between diethyl ether and 1N aqueous hydrochloric acid, the ether phase was dried over sodium sulfate and the solvent mixture was distilled off. Ray yield: 14.4 g. After chromatography on silica gel with trichloromethane/petroleum ether (4:1 parts by volume) as the eluent, 8.2 g (62% of the theoretical amount) 4-hydroxyphenylacetic acid iodopropargyl ester (m.p. 73°-77° C.) were obtained.

Workup

  1. dry with materialthe ether phase was dried over sodium sulfate
  2. distillationthe solvent mixture was distilled off

Sources & evidence

ORD record
ord-f8764f0956ea4c3e8554970058a86720
Source dataset
uspto-grants-1988_03
Patent number
US04731466

Reaction notes

Loading…