Hydrochloric Acid → 4'-Methoxycarbonyloxy-4-biphenylcarboxylic acid

HRID 36132

Reaction equation

HRID 36132 reaction equation
C([C@H:3]([CH2:18][CH2:19][CH2:20][CH2:21]CC1C=CC(O)=CC=1)[CH:4]=[C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11]C(C)(C)C)=[O:10])=[CH:7][CH2:6]1)#N.[OH-:30].[Na+].Cl[C:33]([O:35][CH3:36])=[O:34].Cl>O.C(O)C>[CH3:36][O:35][C:33]([O:30][C:19]1[CH:18]=[CH:3][C:4]([C:5]2[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:16][CH:17]=2)=[CH:21][CH:20]=1)=[O:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 53887099tert-butyl 4-[(2R)-2-cyano-7-(4-hydroxyphenyl)heptylidene]benzoate

Product 1

HCID 183284084'-Methoxycarbonyloxy-4-biphenylcarboxylic acidYield 95.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

4'-Hydroxy-4-biphenylcarboxylic acid (3) (4 g, 18.67 mmol) and sodium hydroxide (1.64 g, 41.1 mmol) were dissolved in water (50 ml) and ethanol (98 ml) at -10° C. To the solution, methyl chloroformate (1.73 ml, 22.4 mmol) was added and the solution was maintained at -5° C. The solution was stirred for 40 minutes and a mixture of water and hydrochloric acid (1:1) was added until the solution became acidic. The solid precipitate was collected by vacuum filtration, washed several times with distilled water and dried to yield 4.72 g (yield 95.5%) of the title compound.

Workup

  1. customat -10° C
  2. additionwas added until the solution
  3. filtrationThe solid precipitate was collected by vacuum filtration
  4. washwashed several times with distilled water
  5. customdried

Sources & evidence

ORD record
ord-233f26ba77eb48bab15e0c1b95234adc
Source dataset
uspto-grants-1995_05
Patent number
US05412144

Linked notes

Loading…