Benzene → HCID 23369392, compound

HRID 2081174Notes

Reaction equation

HRID 2081174 reaction equation
C1C=CC=CC=1.[H-].[Na+].[OH:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.Cl[CH2:17][C:18]([OH:20])=[O:19]>O>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[CH2:10][O:9][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 241Benzene3×HCID 300Chloroacetic AcidHCID 24758Sodium hydrideHCID 694672-Thiophenemethanol

Product 1

HCID 23369392HCID 23369392, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred benzene suspension of NaH (0.39 g, 32.2 mmol) was added a benzene solution of 2-hydroxymethylthiophene (2.0 g, 15.1 mmol). The reaction was stirred 3 h and a benzene solution (10 mL) of chloroacetic acid (1.56 g, 16.6 mmol) was added. The reaction was heated to reflux for 15 h then cooled to room temperature and a small amount of water was cautiously added. The aqueous layer was diluted, separated, acidified and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over MgSO4. Evaporation afforded thien-2-ylmethoxyacetic acid as a tan oil (66%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 h
  3. additionThe aqueous layer was diluted
  4. customseparated
  5. extractionextracted with methylene chloride (3×50 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customEvaporation

Sources & evidence

ORD record
ord-c6775837264e42b993144b8a46862c28
Source dataset
uspto-grants-1993_02
Patent number
US05183818

Reaction notes

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