Benzyl Alcohol → Benzyl 2-Benzylacrylate

HRID 256546

Reaction equation

HRID 256546 reaction equation
[CH2:1]([C:8](=[CH2:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:28](O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCOCC.CN(C)C1C=CN=CC=1>[CH2:1]([C:8](=[CH2:12])[C:9]([O:11][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 3035712-Benzylacrylic Acid

Product 1

HCID 10912012Benzyl 2-Benzylacrylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Benzylacrylic acid (2.20 g, 13.6 mmol) in dry ether (40 mL) was treated with dicyclohexylcarbodiimide (2.60 g, 12.6 mmol), benzyl alcohol (1.30 mL, 12.6 mmol) and 4-dimethylaminopyridine (0.310 g, 2.54 mmol). After stirring at room temperature for 44 h, the mixture was filtered and evaporated. Chromatography of the residue on silica with 5% oil: b.p. 150° C. (0.2 mm); TLC (20% ethyl acetate/80% hexane) Rf =0.31; 1H-NMR (CDCl3) 7.15-7.40 (m, 10H), 6.28 (m, 1H), 5.49 (m, 1H), 5.17 (2H,s), 3.67 (s, 2H).

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-26067147a12c446a8b3a46ae25a1eef9
Source dataset
uspto-grants-1993_11
Patent number
US05258362

Linked notes

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