Carbon Dioxide → HCID 13540118, compound

HRID 1583349Notes

Reaction equation

HRID 1583349 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[S:7][CH:8]=[C:9]([CH3:10])[C:5]=2[CH:4]=1.C([Li])CCC.[C:18](=[O:20])=[O:19]>CCOCC>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[S:7][C:8]([C:18]([OH:20])=[O:19])=[C:9]([CH3:10])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 13540113HCID 13540113, compoundHCID 178418339Butyllithium

Product 1

HCID 13540118HCID 13540118, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5-hydroxymethyl-3-methylbenzo[b]thiophene (8.50 g.) in dry ether (120 ml.) was added dropwise to a stirred solution of n-butyl lithium (72 ml. of 1.6M solution in hexane) in dry ether (120 ml.) at 0° under an atmosphere of dry nitrogen. The resulting mixture was stirred at 0° for 2 hours and then poured onto a mixture of crushed solid carbon dioxide and ether. When all the carbon dioxide had evaporated the mixture was shaken with water. The aqueous layer was separated and acidified with concentrated hydrochloric acid. The solid was filtered off, washed well with water and crystallized from ethanol to give 5-hydroxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid (4.80 g.), m.p. 260°-262°.

Workup

  1. customWhen all the carbon dioxide had evaporated the mixture
  2. stirringwas shaken with water
  3. customThe aqueous layer was separated
  4. filtrationThe solid was filtered off
  5. washwashed well with water
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-198377133f3b4d40935c0a22db809a8e
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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