Methyl Acrylate → Methyl 3-octadecylthiopropionate

HRID 326100Notes

Reaction equation

HRID 326100 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]([SH:38])[CH2:21][CH2:22]CCCCCCCCCCCCCCC.BrCC[C:42](OC)=[O:43].C(OC)(=O)C=C.C[O-].[Na+]>>[CH2:1]([CH2:22][CH2:21][C:20]([O:43][CH3:42])=[S:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 5

HCID 7294Methyl AcrylateHCID 82181-BromooctadecaneHCID 179051-OctadecanethiolHCID 76934Methyl 3-bromopropanoateHCID 10942334Sodium Methoxide

Product 1

HCID 21274870Methyl 3-octadecylthiopropionate

Procedure

Instead of octadecyl bromide, there can also be used octadecyl mercaptan which is then reacted with methyl 3-bromopropionate or added on to methyl acrylate with sodium methylate catalysis. In both cases, methyl 3-octadecylthiopropionate is obtained.

Sources & evidence

ORD record
ord-bb23c62e2ad048e88764e3d13c60ad33
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

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