Methyl Acrylate → HCID 13531084, compound

HRID 1029526Notes

Reaction equation

HRID 1029526 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:14][C:15]([C:18]1[CH:23]=[C:22]([SH:24])[CH:21]=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]=1[OH:29])([CH3:17])[CH3:16]>C(#N)C>[CH3:28][C:25]([C:20]1[CH:21]=[C:22]([S:24][CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH:23]=[C:18]([C:15]([CH3:17])([CH3:16])[CH3:14])[C:19]=1[OH:29])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 13531084HCID 13531084, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl acrylate (1.1 g, 12.6 mmol) and triethylamine (0.5 mL, 0.4 mmol) are sequentially added to a room temperature solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.0 g, 12.6 mmol) in acetonitrile (6 mL). The reaction is stirred for 1.5 hours and then evaporated under high vacuum to give 3.7 g (90%) of the crude product. A small portion is chromatographed on a silica column with ethyl acetate/hexane (1/9) to afford an analytically pure sample of methyl 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoate, mp 64.0°-66.0° C.

Workup

  1. customevaporated under high vacuum
  2. customto give 3.7 g (90%) of the crude product
  3. customA small portion is chromatographed on a silica column with ethyl acetate/hexane (1/9)

Sources & evidence

ORD record
ord-198d928f106547cfa979c438156d7275
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

Loading…