Benzyl Alcohol → Benzyl acrylate

HRID 583793Notes

Reaction equation

HRID 583793 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:16](=[O:19])[CH:17]=[CH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 75617Benzyl acrylateYield 69.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl alcohol (4.76 mL, 0.046 mol), 4-dimethylamino-pyridine (“DMAP,” 0.790 g, 0.0065 mol) and triethylamine (12.85 mL, 0.09297 mol) in dichloromethane (92 mL) was added a solution of acryloyl chloride (7.54 mL, 0.09297 mol) slowly at 0° C., and the mixture was stirred at 0° C. for 2.5 hours. The mixture was quenched with aqueous sodium bicarbonate, and the quenched mixture was extracted with dichloromethane (2×100 mL). The extracts were combined, dried (MgSO4), and rotary evaporated to give a yellow oil. The oil was purified by column chromatography, eluting with hexanes/ethyl acetate (95:5) to give 5.19 g (64%) of acrylic acid benzyl ester as a clear oil.

Workup

  1. customThe mixture was quenched with aqueous sodium bicarbonate
  2. extractionthe quenched mixture was extracted with dichloromethane (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. customrotary evaporated
  5. customto give a yellow oil
  6. customThe oil was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-1f6638c7c5824ad49f0e00a59ddff6ef
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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