Hydrochloric Acid → Benzoic Acid

HRID 373558Notes

Reaction equation

HRID 373558 reaction equation
CC1C2C=C(/C(/C)=C/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)C=CC=2SCCC1.[Na].[OH-].[Na+].Cl>C(O)C.O>[C:19]([OH:21])(=[O:20])[C:18]1[CH:24]=[CH:25][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 19935458HCID 19935458, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 1.2 g of ethyl p-[(E)-2-(2,3,4,5-tetrahydro-5-methyl-1-benzothiepin-7-yl)propenyl]benzoate in 30 ml of ethanol was treated with 5 ml of water which contained 0.8 g of sodium hyohoxide (NaOH). The reaction mixture was stirred at 35° C. overnight, poured on to ice, acidified with HCl and extracted with ether. The organic phase was washed with water, dried and concentrated. After recrystallization from ethyl acetate, there were obtained 885 mg of p-[(E)-2,3,4,5-tetrahydro-5-methyl-1-benzothiepin-7-yl)-ropenyl]benzoic acid in the form of white crystals of melting point 186° C.

Workup

  1. additionpoured on to ice
  2. extractionextracted with ether
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-85d3719aac394b8bb251ee6da2ffbb95
Source dataset
uspto-grants-1992_11
Patent number
US05164387

Reaction notes

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