Methacryloyl chloride → HCID 85980398, compound

HRID 1950664Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([P:13]([OH:16])(=[O:15])[OH:14])[P:9]([OH:12])(=[O:11])[OH:10].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19]>>[C:17]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([P:13]([OH:16])(=[O:14])[OH:15])[P:9]([OH:10])(=[O:12])[OH:11])(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 85980403HCID 85980403, compound

Product 1

HCID 85980398HCID 85980398, compound

Procedure

Following the General Synthetic Procedure B, methyl 6-chlorohexanoate is reacted with tetramethyl methanebisphosphonate to produce tetramethyl 5-methoxycarbonylpentyl-methanebisphosphonate that is then hydrolyzed to yield 5-carboxypentyl-methanebisphosphonic acid, and then hydrogenated to reduce the carboxy group to a hydroxymethylene group. The resulting 6-hydroxyhexyl-methanebisphosphonic acid is then methacrylated with methacryloyl chloride to afford 6-methacryloxyhexyl-methanebisphosphonic acid.

Sources & evidence

ORD record: ord-a8bbef19cd0a461687eb29abc58da695
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404144B2

Reaction notes

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