Naphthalene → 2-Hydroxy-but-3-enoic acid ethyl ester

HRID 1099473Notes

Reaction equation

HRID 1099473 reaction equation
[CH2:1](O)[C@H:2]1[O:7][C@H:6]([O:8][C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H:5]([OH:20])[C@@H:4](O)[C@@H:3]1O.C1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C(C)O>C(O)C>[OH:20][CH:5]([CH:4]=[CH2:3])[C:6]([O:7][CH2:2][CH3:1])=[O:8]

Participants

5

Reactant 3

HCID 931NaphthaleneHCID 5988SucroseHCID 7344Ethyl Lactate

Product 1

HCID 132714822-Hydroxy-but-3-enoic acid ethyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

An autoclave (50 cc microclave) is charged with 8.0 g of ethanol, 0.2252 g of sucrose (0.6578 mmol), 118.9 mg naphthalene (internal standard) and finally with 160.0 mg Sn-BEA (prepared according to U.S. Pat. No. 6,306,364). The autoclave is closed, charged with 20 bar of argon and heated to 160° C. After the temperature reaches 100° C., the mechanical stirrer is started (500 rpm) and the mixture is heated for 20 hours under these conditions. GC-analysis of the reaction mixture shows that 1.03 mmol of ethyl lactate is formed (39%) together with 0.316 mmol ethyl 2-hydroxy-3-butenoate (16%).

Workup

  1. customprepared
  2. customThe autoclave is closed
  3. additioncharged with 20 bar of argon
  4. customreaches 100° C.
  5. temperaturethe mixture is heated for 20 hours under these conditions

Sources & evidence

ORD record
ord-c107c959140b4e37a91e2c840f1f3d4f
Source dataset
uspto-grants-2012_03
Patent number
US08143439B2

Reaction notes

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