Methanesulfonic Acid → HCID 69444019, compound

HRID 388862Notes

Reaction equation

HRID 388862 reaction equation
[CH:1]1([C:11](C2CCCCCCCCC2)(C2CCCCCCCCC2)[OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:33]([OH:37])(=[O:36])[CH:34]=[CH2:35].CS(O)(=O)=O>COC1C=CC(O)=CC=1.CCCCCCC>[C:33]([OH:37])(=[O:36])[CH:34]=[CH2:35].[CH:1]1([CH2:11][OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:1]1([CH2:11][OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:1]1([CH2:11][OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 6581Acrylic AcidHCID 19018363HCID 19018363, compound

Product 1

HCID 69444019HCID 69444019, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 8900HeptaneSolvent

Procedure

To a 500 mL flask equipped with a Dean-Stark trap was added tricyclodecyl methanol (50 g, 300 mmol), acrylic acid (23.8 g, 330 mmol), heptane (250 mL), methanesulfonic acid (3.0 g), and MEHQ (132 mg). The mixture was refluxed for 65 minutes under a mild air sparge, at which point 5.3 mL water (theoretical amount 5.4 mL) had collected in the Dean-Stark trap. The mixture was washed with sodium bicarbonate, dried over magnesium sulfate, and finally passed over silica gel. The solvent was removed by rotary evaporation to afford the product (64.3 g, 97.3% yield).

Workup

  1. customTo a 500 mL flask equipped with a Dean-Stark trap
  2. temperatureThe mixture was refluxed for 65 minutes under a mild air
  3. customsparge, at which
  4. customhad collected in the Dean-Stark trap
  5. washThe mixture was washed with sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-322c78e4be1a4abc8da41609623cc903
Source dataset
uspto-grants-2013_02
Patent number
US08378017B2

Reaction notes

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