Methanol → HCID 54032639, compound

HRID 1493886Notes

Reaction equation

HRID 1493886 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].CO.C[O-].[Na+].Cl[CH:13]=[CH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:19]=1>C(OCC)C>[OH:30][CH:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][CH2:16][CH:15]=[CH:14][CH2:13][S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 65143-Mercaptopropionic AcidHCID 10942334Sodium MethoxideHCID 53900965HCID 53900965, compound

Product 1

HCID 54032639HCID 54032639, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

9.15 ml. (0.105 mole) 3-mercaptopropionic acid are dissolved in 70 ml. methanol and stirred with 315 ml. 1 M sodium methylate solution for 10 minutes at ambient temperature under an atmosphere of nitrogen. Subsequently, 19.79 g. (0.07 mole) 1-chloro-4-[3-(1-hydroxyhexyl)-phenoxy]-but-1-ene in 70 ml. methanol are added dropwise thereto in the course of 15 minutes. The reaction mixture is further stirred for 3 hours a ambient temperature and the solvent is then stripped off. The residue is taken up in diethyl ether and extracted several times with 2 M aqueous sodium hydroxide solution. The aqueous solution is acidified with 2 M hydrochloric acid and the desired compound is extracted with methylene chloride. After drying and stripping off the solvent, there are obtained 22.5 g. (91% of theory) of the title compound in the form of an oil.

Workup

  1. customin the course of 15 minutes
  2. extractionextracted several times with 2 M aqueous sodium hydroxide solution
  3. extractionthe desired compound is extracted with methylene chloride
  4. customAfter drying
  5. customare obtained 22.5 g

Sources & evidence

ORD record
ord-a1ffcd29a6764a1fb030ad3eea6853aa
Source dataset
uspto-grants-1991_06
Patent number
US05025028

Reaction notes

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