Methanol → HCID 54032639, compound

HRID 1164935Notes

Reaction equation

HRID 1164935 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. 1M 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 at ambient temperature and the solvent is then stripped off. The residue is taken up in diethyl ether and extracted several times with 2M aqueous sodium hydroxide solution. The aqueous solution is acidified with 2M 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 2M 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-688fdedc06a14ceea607f037c47305ac
Source dataset
uspto-grants-1990_03
Patent number
US04906666

Reaction notes

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