Hydrochloric Acid → 3-(Octadecylsulfanyl)propanoic acid

HRID 482560Notes

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].[SH:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)(C)C>[CH2:1]([S:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[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

Conditions

Temperature: 80 °C

Procedure

To a solution of 86.8 gm (0.25 mole) octadecyl bromide, 29.2 gm (0.275 mole) 3-mercaptopropionic acid and 90.0 gm isopropanol at 80° C. was added 95.0 gm (0.275 mole) 40% aqueous potassium carbonate solution dropwise. The mixture was heated at 80° C. for 8 hours and then cooled to 60° C. After adding 125.0 gm water and 36.8 gm of 30% hydrochloric acid solution, the mixture was slowly heated to 94° C. while distilling aqueous isopropyl alcohol from the reaction. The product separated as an oil from the aqueous phase. It was isolated using a separatory funnel and washed with hot water. Upon cooling, the product solidified as a light tan waxy solid. It was dried in a vacuum oven at 50° C. to yield 91.35 gm (98%)

Workup

temperaturecooled to 60° C
temperaturethe mixture was slowly heated to 94° C.
distillationwhile distilling aqueous isopropyl alcohol
customfrom the reaction
customThe product separated as an oil from the aqueous phase
customIt was isolated
washwashed with hot water
temperatureUpon cooling
customIt was dried in a vacuum oven at 50° C.
customto yield 91.35 gm (98%)

Sources & evidence

ORD record: ord-65729686de044af895a64a8a5a06a53e
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05798402

Reaction notes

Loading…