Water → HCID 20335004, compound

HRID 1973988Notes

Reaction equation

HRID 1973988 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:9]=[CH:8]2)=O.[OH-].[Na+].O>CO>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20335205HCID 20335205, compound

Product 1

HCID 20335004HCID 20335004, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 25.8 g. of 6-methoxycarbonyl-2-naphthyl-α-methylacetic acid, 4 g. of sodium hydroxide, 10 ml. of water, and 500 ml. of methanol are heated to 50° C, cooled, and evaporated. The residue is taken up in 500 ml. of diethylene glycol dimethyl ether and diborane is bubbled through. The resulting mixture is saturated with diborane and then is allowed to stand for 18 hours. The reaction mixture is acidified by the addition of aqueous 1N hydrochloric acid. The mixture is extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, and evaporated to give 6-hydroxymethyl-2-naphthyl-α-methylacetic acid.

Workup

  1. additionA mixture of 25.8 g
  2. temperaturecooled
  3. customevaporated
  4. customof diethylene glycol dimethyl ether and diborane is bubbled through
  5. additionThe reaction mixture is acidified by the addition of aqueous 1N hydrochloric acid
  6. extractionThe mixture is extracted with methylene chloride
  7. washwashed with water to neutrality
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-26f81790ff2e4093be13b9c649897c9e
Source dataset
uspto-grants-1976_12
Patent number
US03998966

Reaction notes

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