6-Methoxy-alpha-tetralone → HCID 59651944, compound

HRID 221809Notes

Reaction equation

HRID 221809 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.O.[C:15]([OH:19])(=[O:18])[CH:16]=[O:17]>CCOC(C)=O>[OH:17][CH:16]([CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[C:15]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 141126-Methoxy-alpha-tetraloneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59651944HCID 59651944, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-methoxy-1-tetralone (20 g, 114 mmol) and glyoxylic acid monohydrate (10.5 g, 114 mmol) was heated at 120° C. in a melt for 5 min. After slight cooling, EtOAc (100 mL) was carefully added. The solid which precipitated was collected to afford 8.5 g (30%) of hydroxyl-(6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetic acid; Mp 212-214° C., MS m/z 251 (M+H).

Workup

  1. customThe solid which precipitated
  2. customwas collected

Sources & evidence

ORD record
ord-f5cf33632daf4a6cb7ae9887b34ae69f
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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