1-Naphthaleneacetic Acid → HCID 70525452, compound

HRID 354721Notes

Reaction equation

HRID 354721 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[CH2:16][O-:17].[Na+].[C]=O.[Na]>C1(C)C=CC=CC=1>[OH:17][CH:16]=[C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 68621-Naphthaleneacetic AcidHCID 2723922Sodium ethoxideHCID 5360545Sodium2×HCID 178418416HCID 178418416, compound

Product 1

HCID 70525452HCID 70525452, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

174 Parts by weight of the methyl ester of α-naphthylacetic acid, 48.1 parts by weight of sodium ethylate, and 450 parts by weight of toluene were heated to 80° C. under a carbon monoxide pressure of 100 bar. Since the carbon monoxide consumed was replaced, the pressure varied between 90 and 100 bar. Upon completion of the reaction the batch was cooled and the unreacted carbon monoxide pumped off. The suspension of the sodium salt in toluene was added to 1 l of ice water and, after dissolution of the sodium salt, the toluene phase separated. Acidifying the aqueous phase yielded the (gas chromatographically) 99.5% pure methyl ester of α-hydroxymethylene-α-naphthylacetic acid, which had a melting point of from 124° to 126° C.

Workup

  1. customSince the carbon monoxide consumed
  2. customUpon completion of the reaction the batch
  3. temperaturewas cooled
  4. customthe toluene phase separated

Sources & evidence

ORD record
ord-44952c1476424cc1bbddc6fb7e678887
Source dataset
uspto-grants-1983_03
Patent number
US04376866

Reaction notes

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