Benzyl mercaptan → 2-(6-Benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

HRID 22433

Reaction equation

HRID 22433 reaction equation
[O-]CC.[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23].[CH2:24]([SH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([S:31][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 2723922Sodium ethoxideHCID 199302642-(6-Bromohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

Product 1

HCID 199302892-(6-Benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium ethoxide (69 mg sodium, 3 mmol in ethanol 1 ml) was added to a stirred suspension of 2-(6-bromohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde (0.98 g, 3 mmol) and benzyl mercaptan (0.35 g, 3 mmol) in ethanol (10 ml) at room temperature under nitrogen. After 1 hour evaporated, water (10 ml) and 2M sodium hydroxide (2 ml) added and extracted with diethyl ether (10 ml). The extracts were washed with water, dried, filtered and evaporated to an oil (1.12 g). Chromatography on silica eluting with dichloromethane gave 2-(6-benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde as a colourless oil.

Workup

  1. customAfter 1 hour evaporated
  2. additionwater (10 ml) and 2M sodium hydroxide (2 ml) added
  3. extractionextracted with diethyl ether (10 ml)
  4. washThe extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to an oil (1.12 g)

Sources & evidence

ORD record
ord-7f6483fff6624318bcdbcd4153c44add
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Linked notes

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