Guaiacol → HCID 15895676, compound

HRID 1417939Notes

Reaction equation

HRID 1417939 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]1[OH:15])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1O>C1C=CC=CC=1>[CH3:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:15][C@@H:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][CH2:14][C@H:5]1[CH2:4][N:2]([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11776TriphenylphosphineHCID 15727193HCID 15727193, compound

Product 1

HCID 15895676HCID 15895676, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 8.21 g (0.04M) of TRANS-1,2,3,4-tetrahydro-2-(N,N-dimethylaminomethyl)naphthalen-1-ol, 11.54 g (0.044M) of triphenyl phosphine, 5.46 g (0.044M) of 2-methoxyphenol and 100 ml of benzene was stirred and a solution of 7.83 g (0.004M) of 95% diethyl azodicatrboxylate in 25 ml of benzene was added dropwise over 45 minutes. After 2 hours, the mixture was filtered and extracted with cold 3% hydrochloric acid. The acid extracts were made basic with dilute sodium hydroxide and the oil which separated was extracted into ether. The solvent was removed and the residual oil chromatographed on silica gel.

Workup

  1. filtrationthe mixture was filtered
  2. extractionextracted with cold 3% hydrochloric acid
  3. customthe oil which separated
  4. extractionwas extracted into ether
  5. customThe solvent was removed
  6. customthe residual oil chromatographed on silica gel

Sources & evidence

ORD record
ord-392507ad9a7446fdabac8f15f7b66099
Source dataset
uspto-grants-1999_03
Patent number
US05880120

Reaction notes

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