Hydrochloric Acid → 2-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal

HRID 496163

Reaction equation

HRID 496163 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].S[CH:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[CH2:20](N(CC)CC)[CH3:21]>COCCOCCOC>[CH2:20]([C:12]([CH2:13][S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH:17]=[CH:16][CH2:15][CH3:14])[CH:11]=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 1382782-MercaptobenzenemethanolHCID 5251295Mercaptobenzyl alcohol

Product 1

HCID 544309312-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenalYield 484.6%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 5.0 g (0.036 mole) of 2-mercaptobenzyl alcohol, 6.4 g (0.032 mole) of 1, 3.6 g (0.036 mole) of triethylamine and 25 mL of 2-methoxyethyl ether was held at reflux for 7 h. Additional 1.1 g of mercaptobenzyl alcohol and 0.72 g of triethylamine was added to the reaction mixture and the mixture was held at reflux for additional 16 h. The reaction mixture was cooled and poured into 6N HCl and extracted with methylene chloride. The methylene chloride extract was wasted twice with 10% NaOH, dried over MgSO4 and concentrated in vacto to give 9.6 g of residue. Purification by HPLC (20% EtOAc-hexane) gave 3.7 g (41%) of 16 as an oil.

Workup

  1. temperatureat reflux for 7 h
  2. temperatureat reflux for additional 16 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacto

Sources & evidence

ORD record
ord-346d294e4065472690ba939724fcfb29
Source dataset
uspto-grants-2005_09
Patent number
US06943189B2

Linked notes

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