Carbon Dioxide → HCID 20260908, compound

HRID 1583353Notes

Reaction equation

HRID 1583353 reaction equation
Br[C:2]1[C:3]2[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:4]=2[S:5][C:6]=1[CH3:7].C([Li])CCC.[C:19](=[O:21])=[O:20]>CCOCC>[OH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:3]2[C:2]([C:19]([OH:21])=[O:20])=[C:6]([CH3:7])[S:5][C:4]=2[CH:8]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 20260931HCID 20260931, compoundHCID 178418339Butyllithium

Product 1

HCID 20260908HCID 20260908, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of 3-bromo-6-hydroxymethyl-2-methylbenzo[b]thiophene (2.11 g.) in dry ether (150 ml.) was added dropwise over 20 minutes to a stirred solution of n-butyl lithium (25 ml. of 1.5M solution in hexane) in dry ether (150 ml.) at -70° C. under an atmosphere of dry nitrogen. The mixture was stirred at -70° C. 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 and the aqueous layer was separated and acidified with concentrated hydrochloric acid. The solid was filtered off, washed well with water and dried to give 6-hydroxymethyl-2-methylbenzo[b]thiophene-3-carboxylic acid (1.26 g.), m.p. 195°-196° C., raised to 196°-197° C. on crystallization from ethanol/water.

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. customdried

Sources & evidence

ORD record
ord-12cc7eda197a42578aee70c6f1983f51
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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