Water → 5-Benzoyloxybenzocyclobutene-1-carboxylic acid methyl ester

HRID 1248364Notes

Reaction equation

HRID 1248364 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].C(N(CC)CC)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 536353185-Hydroxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 542092825-Benzoyloxybenzocyclobutene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27 g of 5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester are dissolved in 2000 ml of dichloromethane and then 18 g of triethylamine are added. Over a period of 5 minutes, while stirring at 10°-20°, 25 g of benzoyl chloride are added in portions, stirring is carried out for 5 hours at room temperature, 200 ml of water are added and the organic phase is separated off, dried over magnesium sulphate and concentrated to dryness by evaporation. 5-benzoyloxybenzocyclobutene-1-carboxylic acid methyl ester is obtained in the form of a colourless, viscous oil.

Workup

  1. stirringstirring
  2. waitis carried out for 5 hours at room temperature
  3. customthe organic phase is separated off
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-87292491e2a74d19912c5bafa1277a27
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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