Methacrylic Acid → HCID 178454696, compound

HRID 1249962Notes

Reaction equation

C(N(CC)CC)C.CS(Cl)(=O)=O.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[CH2:15].O[CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH:41]=[O:42])=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:25][CH2:24]1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:15][C:14](=[CH2:16])[C:13]([O:18][CH2:20][CH2:21][CH2:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH:41]=[O:42])=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:27][CH2:28]1)=[O:17]

Participants

Conditions

Temperature: -25 °C

Procedure

Firstly 9.4 ml of triethylamine and then 2.63 ml of methanesulphonyl chloride were added dropwise at −25° C. to a solution of 2.9 ml of methacrylic acid in 30 ml of tetrahydrofuran. Thereafter, the mixture was stirred at −25° C. for 1 hour and then a solution of 9.9 g of trans-4′-[4-(3-hydroxy-propyl)-cyclohexyl]-biphenyl-4-carboxaldehyde and 1.1 g of 4-dimethylamino-pyridine in 50 ml of tetrahydrofuran was added dropwise. Thereafter, the mixture was left to react at 0° C. for 2.5 hours and then at room temperature for 18 hours. Thereupon, the reaction mixture was filtered over Celite, the filtrate was partitioned between ether and water, the ether phase was dried over magnesium sulphate and evaporated. This gave 11.5 g of crude trans-4′-[4-[3-(2-methyl-acryloyloxy)-propyl]-cyclohexyl]-biphenyl-4-carboxaldehyde in solid form.

Workup

waitThereafter, the mixture was left
customto react at 0° C. for 2.5 hours
waitat room temperature for 18 hours
filtrationThereupon, the reaction mixture was filtered over Celite
customthe filtrate was partitioned between ether and water
dry with materialthe ether phase was dried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-70812e9a4b2548e9a4f211b2f4c0ed7b
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335409B1

Reaction notes

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