Sulfuric Acid → HCID 54066414, compound

HRID 1613481Notes

Reaction equation

HRID 1613481 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][C:12](=[CH2:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18](=[CH2:20])[CH3:19].S(=O)(=O)(O)O>ClCCl>[C:18]([O:14][C:13](=[O:15])[C:12]([CH2:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[CH2:16])([CH3:20])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 113219674-(Benzyloxy)-2-methylidene-4-oxobutanoic acid

Product 1

HCID 54066414HCID 54066414, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(benzyloxycarbonylmethyl)propenoic acid (25.0 g, 114.0 mmole) in dichloromethane (200 ml) at -78° C. was added condensed isobutylene (50 ml) and concentrated sulphuric acid (1 ml). The mixture was allowed to warm to room temperature and kept for 72 hours. After this time the solution was washed with 10% sodium carbonate solution (3×200 ml), dried over magnesium sulphate and evaporated to give the required ester as a pale yellow oil (28.4 g, 90%). Found: C,69.60; H,7.35. C16H20O4 requires: C,69.55; H,7.30%.

Workup

  1. washAfter this time the solution was washed with 10% sodium carbonate solution (3×200 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-d0f197f5f6844444b8be1e128cf64c75
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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