Carbon Dioxide → HCID 23320901, compound

HRID 280609Notes

Reaction equation

HRID 280609 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:12])[C:6]=2[CH:13]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>CCOCC>[OH:11][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:19]([OH:21])=[O:20])=[CH:13][C:6]=2[C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 23320893HCID 23320893, compoundHCID 178418339Butyllithium

Product 1

HCID 23320901HCID 23320901, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5-bromo-2-hydroxymethyl-3-methylbenzofuran (Annalen, 1112, 1973) (1.93 g) in dry ether (50 ml) was added dropwise to a stirred solution of n-butyl-lithium (12.90 ml of 1.55M solution in hexane) in dry ether (50 ml) at 0° C. under an atmosphere of dry nitrogen. The 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, washed with ether and acidified with concentrated hydrochloric acid. The solid was filtered off, washed with water, dried and crystallised from isopropanol/petrol (b.p. 80°-100°) to give 2-hydroxymethyl-3-methylbenzofuran-5-carboxylic acid (0.50 g), m.p. 220°-222°.

Workup

  1. customWhen all the carbon dioxide had evaporated the mixture
  2. stirringwas shaken with water
  3. customThe aqueous layer was separated
  4. washwashed with ether
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customdried
  8. customcrystallised from isopropanol/petrol (b.p. 80°-100°)

Sources & evidence

ORD record
ord-c6d7501ae5e949dfbd216ecb07f0c834
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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