3-Chlorobenzoic Acid → 3-Chlorobenzoyl 1-methyl-1-propyl carbonate

HRID 398261Notes

Reaction equation

HRID 398261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl[C:14]([O:16][CH:17]([CH2:19][CH3:20])[CH3:18])=[O:15]>O>[C:14](=[O:15])([O:16][CH:17]([CH3:18])[CH2:19][CH3:20])[O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 11829505sec-Butyl chloroformate

Product 1

HCID 865913903-Chlorobenzoyl 1-methyl-1-propyl carbonateYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well-stirred reaction vessel equipped with a thermometer and a pH electrode were added 39 g of water and 0.20 g of Arquad CB50 at 5° C. After the addition of 0.05 mole of 3-chlorobenzoic acid the pH was adjusted to 6 using a 10 wt % aqueous NaOH solution. Then, 0.05 mole of sec-butyl chloroformate was dosed within 5 min at 5° C. During this time and a post-reaction time of 165 min at 5° C. the pH was kept at a value between 6 and 9. The reaction mixture was allowed to separate, giving 12.5 g of 3-chlorobenzoyl 1-methyl-1-propyl carbonate having a content of 98% in a yield of 95%.

Workup

  1. customTo a well-stirred reaction vessel
  2. customequipped with a thermometer
  3. customa post-reaction time of 165 min
  4. customat 5° C.
  5. customto separate

Sources & evidence

ORD record
ord-08e8848c0b2c4f53a157200aa871f770
Source dataset
uspto-grants-2003_08
Patent number
US06610880B1

Reaction notes

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